JP2016098210A - 2-alkoxy-5-(trifluoromethyl)pyrimidine derivative and method for producing the same - Google Patents
2-alkoxy-5-(trifluoromethyl)pyrimidine derivative and method for producing the same Download PDFInfo
- Publication number
- JP2016098210A JP2016098210A JP2014237928A JP2014237928A JP2016098210A JP 2016098210 A JP2016098210 A JP 2016098210A JP 2014237928 A JP2014237928 A JP 2014237928A JP 2014237928 A JP2014237928 A JP 2014237928A JP 2016098210 A JP2016098210 A JP 2016098210A
- Authority
- JP
- Japan
- Prior art keywords
- pyrimidine
- trifluoromethyl
- methyl
- amino
- butoxy
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
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- 238000004519 manufacturing process Methods 0.000 title claims abstract description 13
- 229910052751 metal Inorganic materials 0.000 claims abstract description 12
- 239000002184 metal Substances 0.000 claims abstract description 12
- GPNLIJCOIGHUQD-UHFFFAOYSA-N 2-phenylmethoxy-5-(trifluoromethyl)pyrimidine Chemical class C(C1=CC=CC=C1)OC1=NC=C(C=N1)C(F)(F)F GPNLIJCOIGHUQD-UHFFFAOYSA-N 0.000 claims abstract description 9
- 150000004703 alkoxides Chemical class 0.000 claims abstract description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 13
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 125000006165 cyclic alkyl group Chemical group 0.000 claims description 4
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 125000004122 cyclic group Chemical group 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 abstract description 22
- 150000001875 compounds Chemical class 0.000 abstract description 9
- 239000003905 agrochemical Substances 0.000 abstract description 3
- 239000012776 electronic material Substances 0.000 abstract description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 444
- -1 substituted-5- (trifluoromethyl) pyrimidine Chemical class 0.000 description 331
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 45
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 36
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 33
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
- 239000012043 crude product Substances 0.000 description 23
- ZQBFAOFFOQMSGJ-UHFFFAOYSA-N hexafluorobenzene Chemical compound FC1=C(F)C(F)=C(F)C(F)=C1F ZQBFAOFFOQMSGJ-UHFFFAOYSA-N 0.000 description 18
- 239000000243 solution Substances 0.000 description 18
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 17
- 238000005481 NMR spectroscopy Methods 0.000 description 16
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 14
- AVTHDZMBGIZIPD-UHFFFAOYSA-N COC1=NC=C(C(=N1)N(C)C1=CC=CC=C1)C(F)(F)F Chemical compound COC1=NC=C(C(=N1)N(C)C1=CC=CC=C1)C(F)(F)F AVTHDZMBGIZIPD-UHFFFAOYSA-N 0.000 description 14
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 13
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 description 12
- SUHGANDNTPOCSQ-UHFFFAOYSA-N N-methyl-N-phenyl-2-phenylmethoxy-5-(trifluoromethyl)pyrimidin-4-amine Chemical compound CN(c1ccccc1)c1nc(OCc2ccccc2)ncc1C(F)(F)F SUHGANDNTPOCSQ-UHFFFAOYSA-N 0.000 description 12
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 9
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 9
- 238000002360 preparation method Methods 0.000 description 9
- BQDJLAWUTBCDHK-UHFFFAOYSA-N 2-(trifluoromethyl)pyrimidine Chemical compound FC(F)(F)C1=NC=CC=N1 BQDJLAWUTBCDHK-UHFFFAOYSA-N 0.000 description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
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- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 7
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- 235000019270 ammonium chloride Nutrition 0.000 description 7
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 7
- 229920006395 saturated elastomer Polymers 0.000 description 7
- 229910052938 sodium sulfate Inorganic materials 0.000 description 7
- 235000011152 sodium sulphate Nutrition 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 238000000605 extraction Methods 0.000 description 6
- WRIKHQLVHPKCJU-UHFFFAOYSA-N sodium bis(trimethylsilyl)amide Chemical compound C[Si](C)(C)N([Na])[Si](C)(C)C WRIKHQLVHPKCJU-UHFFFAOYSA-N 0.000 description 6
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- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 description 4
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- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 4
- 239000002994 raw material Substances 0.000 description 4
- 239000000741 silica gel Substances 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
- 238000004809 thin layer chromatography Methods 0.000 description 4
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 description 3
- CPCHRGFQWZMVNX-UHFFFAOYSA-N 5-(trifluoromethyl)pyrimidine Chemical class FC(F)(F)C1=CN=CN=C1 CPCHRGFQWZMVNX-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
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- 125000006276 2-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C(*)C([H])=C1[H] 0.000 description 2
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- 208000033962 Fontaine progeroid syndrome Diseases 0.000 description 1
- GNDSIQFCWKHCSI-UHFFFAOYSA-N N-(2-butoxy-3-ethylphenyl)-N-methyl-5-(trifluoromethyl)pyrimidin-4-amine Chemical compound C(CCC)OC1=C(C=CC=C1CC)N(C)C1=NC=NC=C1C(F)(F)F GNDSIQFCWKHCSI-UHFFFAOYSA-N 0.000 description 1
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- WPZUKTYIYBCMEV-UHFFFAOYSA-N N-(3-butoxyphenyl)-2-ethoxy-N-methyl-5-(trifluoromethyl)pyrimidin-4-amine N-(3-butoxyphenyl)-N-methyl-2-propoxy-5-(trifluoromethyl)pyrimidin-4-amine Chemical compound C(CC)OC1=NC=C(C(=N1)N(C)C1=CC(=CC=C1)OCCCC)C(F)(F)F.C(C)OC1=NC=C(C(=N1)N(C)C1=CC(=CC=C1)OCCCC)C(F)(F)F WPZUKTYIYBCMEV-UHFFFAOYSA-N 0.000 description 1
- ZDLJDDOAOPCHEB-UHFFFAOYSA-N N-(3-iodo-2-propoxyphenyl)-N-methyl-5-(trifluoromethyl)pyrimidin-4-amine Chemical compound C(CC)OC1=C(C=CC=C1I)N(C)C1=NC=NC=C1C(F)(F)F ZDLJDDOAOPCHEB-UHFFFAOYSA-N 0.000 description 1
- HZDOIXGDSJLWIQ-UHFFFAOYSA-N N-(4-bromophenyl)-2-cyclopentyloxy-N-methyl-5-(trifluoromethyl)pyrimidin-4-amine N-(4-bromophenyl)-2-hexoxy-N-methyl-5-(trifluoromethyl)pyrimidin-4-amine Chemical compound C(CCCCC)OC1=NC=C(C(=N1)N(C)C1=CC=C(C=C1)Br)C(F)(F)F.C1(CCCC1)OC1=NC=C(C(=N1)N(C)C1=CC=C(C=C1)Br)C(F)(F)F HZDOIXGDSJLWIQ-UHFFFAOYSA-N 0.000 description 1
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- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 150000001448 anilines Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 235000019445 benzyl alcohol Nutrition 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000002933 cyclohexyloxy group Chemical group C1(CCCCC1)O* 0.000 description 1
- XTLQJDSCZZMTFE-UHFFFAOYSA-N cyclohexyloxycyclohexane;lithium Chemical compound [Li].C1CCCCC1OC1CCCCC1 XTLQJDSCZZMTFE-UHFFFAOYSA-N 0.000 description 1
- AKOUBXPJKXUSKX-UHFFFAOYSA-N cyclohexyloxycyclohexane;potassium Chemical compound [K].C1CCCCC1OC1CCCCC1 AKOUBXPJKXUSKX-UHFFFAOYSA-N 0.000 description 1
- XZDNOKDWXGNNKZ-UHFFFAOYSA-N cyclohexyloxycyclohexane;sodium Chemical compound [Na].C1CCCCC1OC1CCCCC1 XZDNOKDWXGNNKZ-UHFFFAOYSA-N 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001887 cyclopentyloxy group Chemical group C1(CCCC1)O* 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000004210 ether based solvent Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 125000002510 isobutoxy group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])O* 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 229960004592 isopropanol Drugs 0.000 description 1
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- YNESATAKKCNGOF-UHFFFAOYSA-N lithium bis(trimethylsilyl)amide Chemical compound [Li+].C[Si](C)(C)[N-][Si](C)(C)C YNESATAKKCNGOF-UHFFFAOYSA-N 0.000 description 1
- JILPJDVXYVTZDQ-UHFFFAOYSA-N lithium methoxide Chemical compound [Li+].[O-]C JILPJDVXYVTZDQ-UHFFFAOYSA-N 0.000 description 1
- WBIUOUBFNXEKBA-UHFFFAOYSA-N lithium;2-methylpropan-1-olate Chemical compound [Li]OCC(C)C WBIUOUBFNXEKBA-UHFFFAOYSA-N 0.000 description 1
- LTRVAZKHJRYLRJ-UHFFFAOYSA-N lithium;butan-1-olate Chemical compound [Li+].CCCC[O-] LTRVAZKHJRYLRJ-UHFFFAOYSA-N 0.000 description 1
- XMAFBJJKWTWLJP-UHFFFAOYSA-N lithium;butan-2-olate Chemical compound [Li+].CCC(C)[O-] XMAFBJJKWTWLJP-UHFFFAOYSA-N 0.000 description 1
- AZVCGYPLLBEUNV-UHFFFAOYSA-N lithium;ethanolate Chemical compound [Li+].CC[O-] AZVCGYPLLBEUNV-UHFFFAOYSA-N 0.000 description 1
- HAUKUGBTJXWQMF-UHFFFAOYSA-N lithium;propan-2-olate Chemical compound [Li+].CC(C)[O-] HAUKUGBTJXWQMF-UHFFFAOYSA-N 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 1
- 125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- SKTCDJAMAYNROS-UHFFFAOYSA-N methoxycyclopentane Chemical compound COC1CCCC1 SKTCDJAMAYNROS-UHFFFAOYSA-N 0.000 description 1
- 125000006606 n-butoxy group Chemical group 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001298 n-hexoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000003935 n-pentoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003506 n-propoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229960005235 piperonyl butoxide Drugs 0.000 description 1
- IUBQJLUDMLPAGT-UHFFFAOYSA-N potassium bis(trimethylsilyl)amide Chemical compound C[Si](C)(C)N([K])[Si](C)(C)C IUBQJLUDMLPAGT-UHFFFAOYSA-N 0.000 description 1
- RPDAUEIUDPHABB-UHFFFAOYSA-N potassium ethoxide Chemical compound [K+].CC[O-] RPDAUEIUDPHABB-UHFFFAOYSA-N 0.000 description 1
- BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- CBMSDILKECEMOT-UHFFFAOYSA-N potassium;2-methylpropan-1-olate Chemical compound [K+].CC(C)C[O-] CBMSDILKECEMOT-UHFFFAOYSA-N 0.000 description 1
- MKNZKCSKEUHUPM-UHFFFAOYSA-N potassium;butan-1-ol Chemical compound [K+].CCCCO MKNZKCSKEUHUPM-UHFFFAOYSA-N 0.000 description 1
- ZUPDNLCLXSWMAE-UHFFFAOYSA-N potassium;butan-2-olate Chemical compound [K+].CCC(C)[O-] ZUPDNLCLXSWMAE-UHFFFAOYSA-N 0.000 description 1
- AWDMDDKZURRKFG-UHFFFAOYSA-N potassium;propan-1-olate Chemical compound [K+].CCC[O-] AWDMDDKZURRKFG-UHFFFAOYSA-N 0.000 description 1
- WQKGAJDYBZOFSR-UHFFFAOYSA-N potassium;propan-2-olate Chemical compound [K+].CC(C)[O-] WQKGAJDYBZOFSR-UHFFFAOYSA-N 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- IKNCGYCHMGNBCP-UHFFFAOYSA-N propan-1-olate Chemical compound CCC[O-] IKNCGYCHMGNBCP-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 125000005920 sec-butoxy group Chemical group 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- JYCDILBEUUCCQD-UHFFFAOYSA-N sodium;2-methylpropan-1-olate Chemical compound [Na+].CC(C)C[O-] JYCDILBEUUCCQD-UHFFFAOYSA-N 0.000 description 1
- SYXYWTXQFUUWLP-UHFFFAOYSA-N sodium;butan-1-olate Chemical compound [Na+].CCCC[O-] SYXYWTXQFUUWLP-UHFFFAOYSA-N 0.000 description 1
- VSCLJRSWEGZJNY-UHFFFAOYSA-N sodium;butan-2-olate Chemical compound [Na+].CCC(C)[O-] VSCLJRSWEGZJNY-UHFFFAOYSA-N 0.000 description 1
- RCOSUMRTSQULBK-UHFFFAOYSA-N sodium;propan-1-olate Chemical compound [Na+].CCC[O-] RCOSUMRTSQULBK-UHFFFAOYSA-N 0.000 description 1
- WBQTXTBONIWRGK-UHFFFAOYSA-N sodium;propan-2-olate Chemical compound [Na+].CC(C)[O-] WBQTXTBONIWRGK-UHFFFAOYSA-N 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Landscapes
- Plural Heterocyclic Compounds (AREA)
Abstract
Description
本発明は、新規な2−アルコキシ−5−(トリフルオロメチル)ピリミジン誘導体及びその製造方法に関する。本発明の2−アルコキシ−5−(トリフルオロメチル)ピリミジン誘導体は各種、医農薬や電子材料の合成原料として有用な化合物である。 The present invention relates to a novel 2-alkoxy-5- (trifluoromethyl) pyrimidine derivative and a method for producing the same. The 2-alkoxy-5- (trifluoromethyl) pyrimidine derivative of the present invention is a useful compound as a synthetic raw material for various medical and agricultural chemicals and electronic materials.
従来より、本発明の2−アルコキシ−5−(トリフルオロメチル)ピリミジン誘導体及びその製造方法は知られていない。
類似の化合物として、2−(4−ニトロフェノキシ)−4−クロロ−5−(トリフルオロメチル)ピリミジン(特許文献1)並びに2−メトキシ−4−クロロ−5−(トリフルオロメチル)ピリミジン(特許文献2)が知られている。
Conventionally, the 2-alkoxy-5- (trifluoromethyl) pyrimidine derivative of the present invention and the production method thereof have not been known.
As similar compounds, 2- (4-nitrophenoxy) -4-chloro-5- (trifluoromethyl) pyrimidine (Patent Document 1) and 2-methoxy-4-chloro-5- (trifluoromethyl) pyrimidine (Patent Document 1) Document 2) is known.
しかしながら、特許文献1及び特許文献2で開示されている類似化合物は、さらにピリミジン環上の4−位にアニリン誘導体を導入した化合物及びその製造方法は記載されていない。 However, as for the similar compounds disclosed in Patent Document 1 and Patent Document 2, a compound in which an aniline derivative is further introduced into the 4-position on the pyrimidine ring and a method for producing the same are not described.
本発明は、5−(トリフルオロメチル)ピリミジン誘導体の合成原料として有用な、2−位がアルコキシ基で置換され、かつ4−位がアミノ基で置換された新規な2−アルコキシ−4−アミノ置換−5−(トリフルオロメチル)ピリミジン誘導体及びその製造方法の提供にある。 The present invention is a novel 2-alkoxy-4-amino substituted with an alkoxy group at the 2-position and substituted with an amino group at the 2-position, which is useful as a raw material for synthesizing 5- (trifluoromethyl) pyrimidine derivatives. The object is to provide a substituted-5- (trifluoromethyl) pyrimidine derivative and a method for producing the same.
本発明者らは、2−ベンジルオキシ−4−アミノ置換−5−(トリフルオロメチル)ピリミジン誘導体を原料とし、各種金属アルコキシドを反応させることにより、本発明の2−アルコキシ−4−アミノ置換−5−(トリフルオロメチル)ピリミジン誘導体が得られることを見出し、本発明を完成させるに至った。
すなわち本発明は、下記一般式(1)
The present inventors use 2-benzyloxy-4-amino-substituted-5- (trifluoromethyl) pyrimidine derivatives as raw materials and react with various metal alkoxides to produce 2-alkoxy-4-amino-substituted- The inventors have found that a 5- (trifluoromethyl) pyrimidine derivative can be obtained, and have completed the present invention.
That is, the present invention provides the following general formula (1)
(式(1)中、R1は、水素原子、メチル基、エチル基、炭素数3〜6の直鎖若しくは分岐若しくは環式のアルキル基、メトキシ基、エトキシ基、炭素数3〜6の直鎖若しくは分岐若しくは環式のアルキルオキシ基、ハロゲン原子、シアノ基又はニトロ基を示し、R2はメチル基、エチル基又は炭素数3〜6の直鎖若しくは分岐若しくは環式のアルキル基を示し、R2がベンジル基であることはない)
で表される2−アルコキシ−5−(トリフルオロメチル)ピリミジン誘導体に係るものである。
(In the formula (1), R 1 represents a hydrogen atom, a methyl group, an ethyl group, a linear or branched or cyclic alkyl group having 3 to 6 carbon atoms, a methoxy group, an ethoxy group, and a straight chain having 3 to 6 carbon atoms. A chain or branched or cyclic alkyloxy group, a halogen atom, a cyano group or a nitro group; R 2 represents a methyl group, an ethyl group or a linear or branched or cyclic alkyl group having 3 to 6 carbon atoms; R 2 is never a benzyl group)
It relates to a 2-alkoxy-5- (trifluoromethyl) pyrimidine derivative represented by:
またその製造方法にあたっては、下記一般式(2) In the production method, the following general formula (2)
(式(2)中、Phはフェニル基を示し、R1は前記式(1)に同じ)
で表わされる2−ベンジルオキシ−5−(トリフルオロメチル)ピリミジン誘導体と、下記一般式(3)
R2O−Metal (3)
(式(3)中、Metalは金属を示し、R2は前記式(1)に同じ)
で表わされる金属アルコキシドとを、反応させる製造方法を提供するものである。
(In the formula (2), Ph represents a phenyl group, and R 1 is the same as the formula (1)).
2-benzyloxy-5- (trifluoromethyl) pyrimidine derivative represented by the following general formula (3)
R 2 O-Metal (3)
(In the formula (3), Metal represents a metal, and R 2 is the same as the formula (1)).
The manufacturing method which makes the metal alkoxide represented by these react is provided.
本発明により、医農薬の合成原料として有用な新規な2−アルコキシ−5−(トリフルオロメチル)ピリミジン誘導体及びその製造方法が提供できる。 INDUSTRIAL APPLICABILITY According to the present invention, a novel 2-alkoxy-5- (trifluoromethyl) pyrimidine derivative useful as a synthetic raw material for medical and agricultural chemicals and a method for producing the same can be provided.
以下、本発明を詳細に説明する。
本発明の一般式(1)で表わされる2−アルコキシ−5−(トリフルオロメチル)ピリミジン誘導体でR1が水素原子である化合物としては、具体的には例えば、2−メトキシ−4−(N−メチルフェニルアミノ)−5−(トリフルオロメチル)ピリミジン、2−エトキシ−4−(N−メチルフェニルアミノ)−5−(トリフルオロメチル)ピリミジン、2−n−プロポキシ−4−(N−メチルフェニルアミノ)−5−(トリフルオロメチル)ピリミジン、2−iso−プロポキシ−4−(N−メチルフェニルアミノ)−5−(トリフルオロメチル)ピリミジン、2−n−ブトキシ−4−(N−メチルフェニルアミノ)−5−(トリフルオロメチル)ピリミジン、2−iso−ブトキシ−4−(N−メチルフェニルアミノ)−5−(トリフルオロメチル)ピリミジン、2−sec−ブトキシ−4−(N−メチルフェニルアミノ)−5−(トリフルオロメチル)ピリミジン、2−tert−ブトキシ−4−(N−メチルフェニルアミノ)−5−(トリフルオロメチル)ピリミジン、2−n−ペントキシ−4−(N−メチルフェニルアミノ)−5−(トリフルオロメチル)ピリミジン、2−cyclo−ペントキシ−4−(N−メチルフェニルアミノ)−5−(トリフルオロメチル)ピリミジン、2−n−ヘキシルオキシ−4−(N−メチルフェニルアミノ)−5−(トリフルオロメチル)ピリミジン、2−cyclo−ヘキシルオキシ−4−(N−メチルフェニルアミノ)−5−(トリフルオロメチル)ピリミジン等が挙げられる。
Hereinafter, the present invention will be described in detail.
Specific examples of the 2-alkoxy-5- (trifluoromethyl) pyrimidine derivative represented by the general formula (1) of the present invention in which R 1 is a hydrogen atom include 2-methoxy-4- (N -Methylphenylamino) -5- (trifluoromethyl) pyrimidine, 2-ethoxy-4- (N-methylphenylamino) -5- (trifluoromethyl) pyrimidine, 2-n-propoxy-4- (N-methyl) Phenylamino) -5- (trifluoromethyl) pyrimidine, 2-iso-propoxy-4- (N-methylphenylamino) -5- (trifluoromethyl) pyrimidine, 2-n-butoxy-4- (N-methyl) Phenylamino) -5- (trifluoromethyl) pyrimidine, 2-iso-butoxy-4- (N-methylphenylamino) -5- (trifluoro) (Romethyl) pyrimidine, 2-sec-butoxy-4- (N-methylphenylamino) -5- (trifluoromethyl) pyrimidine, 2-tert-butoxy-4- (N-methylphenylamino) -5- (trifluoro Methyl) pyrimidine, 2-n-pentoxy-4- (N-methylphenylamino) -5- (trifluoromethyl) pyrimidine, 2-cyclo-pentoxy-4- (N-methylphenylamino) -5- (trifluoro Methyl) pyrimidine, 2-n-hexyloxy-4- (N-methylphenylamino) -5- (trifluoromethyl) pyrimidine, 2-cyclo-hexyloxy-4- (N-methylphenylamino) -5- ( (Trifluoromethyl) pyrimidine and the like.
本発明の一般式(1)で表わされる2−アルコキシ−5−(トリフルオロメチル)ピリミジン誘導体でR1がメチル基である化合物としては、具体的には例えば、2−メトキシ−4−[N−メチル−(2−メチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−エトキシ−4−[N−メチル−(2−メチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−プロポキシ−4−[N−メチル−(2−メチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−iso−プロポキシ−4−[N−メチル−(2−メチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ブトキシ−4−[N−メチル−(2−メチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−iso−ブトキシ−4−[N−メチル−(2−メチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−sec−ブトキシ−4−[N−メチル−(2−メチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−tert−ブトキシ−4−[N−メチル−(2−メチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ペントキシ−4−[N−メチル−(2−メチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−cyclo−ペントキシ−4−[N−メチル−(2−メチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ヘキシルオキシ−4−[N−メチル−(2−メチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−cyclo−ヘキシルオキシ−4−[N−メチル−(2−メチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−メトキシ−4−[N−メチル−(3−メチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−エトキシ−4−[N−メチル−(3−メチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−プロポキシ−4−[N−メチル−(3−メチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−iso−プロポキシ−4−[N−メチル−(3−メチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ブトキシ−4−[N−メチル−(3−メチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−iso−ブトキシ−4−[N−メチル−(3−メチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−sec−ブトキシ−4−[N−メチル−(3−メチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−tert−ブトキシ−4−[N−メチル−(3−メチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ペントキシ−4−[N−メチル−(3−メチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−cyclo−ペントキシ−4−[N−メチル−(3−メチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ヘキシルオキシ−4−[N−メチル−(3−メチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−cyclo−ヘキシルオキシ−4−[N−メチル−(3−メチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−メトキシ−4−[N−メチル−(4−メチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−エトキシ−4−[N−メチル−(4−メチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−プロポキシ−4−[N−メチル−(4−メチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−iso−プロポキシ−4−[N−メチル−(4−メチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ブトキシ−4−[N−メチル−(4−メチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−iso−ブトキシ−4−[N−メチル−(4−メチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−sec−ブトキシ−4−[N−メチル−(4−メチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−tert−ブトキシ−4−[N−メチル−(4−メチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ペントキシ−4−[N−メチル−(4−メチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−cyclo−ペントキシ−4−[N−メチル−(4−メチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ヘキシルオキシ−4−[N−メチル−(4−メチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−cyclo−ヘキシルオキシ−4−[N−メチル−(4−メチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン等が挙げられる。 Specific examples of the 2-alkoxy-5- (trifluoromethyl) pyrimidine derivative represented by the general formula (1) of the present invention in which R 1 is a methyl group include 2-methoxy-4- [N -Methyl- (2-methylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-ethoxy-4- [N-methyl- (2-methylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-propoxy-4- [N-methyl- (2-methylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-iso-propoxy-4- [N-methyl- (2-methylphenyl) Amino] -5- (trifluoromethyl) pyrimidine, 2-n-butoxy-4- [N-methyl- (2-methylphenyl) amino] -5- (trifluoromethyl) pi Midine, 2-iso-butoxy-4- [N-methyl- (2-methylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-sec-butoxy-4- [N-methyl- (2-methyl) Phenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-tert-butoxy-4- [N-methyl- (2-methylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-pentoxy -4- [N-methyl- (2-methylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-cyclo-pentoxy-4- [N-methyl- (2-methylphenyl) amino] -5 (Trifluoromethyl) pyrimidine, 2-n-hexyloxy-4- [N-methyl- (2-methylphenyl) amino] -5- (trifluoromethyl) pi Limidine, 2-cyclo-hexyloxy-4- [N-methyl- (2-methylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-methoxy-4- [N-methyl- (3-methylphenyl) ) Amino] -5- (trifluoromethyl) pyrimidine, 2-ethoxy-4- [N-methyl- (3-methylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-propoxy-4- [N-methyl- (3-methylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-iso-propoxy-4- [N-methyl- (3-methylphenyl) amino] -5- (trifluoro Methyl) pyrimidine, 2-n-butoxy-4- [N-methyl- (3-methylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-i o-butoxy-4- [N-methyl- (3-methylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-sec-butoxy-4- [N-methyl- (3-methylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-tert-butoxy-4- [N-methyl- (3-methylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-pentoxy-4- [ N-methyl- (3-methylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-cyclo-pentoxy-4- [N-methyl- (3-methylphenyl) amino] -5- (trifluoromethyl ) Pyrimidine, 2-n-hexyloxy-4- [N-methyl- (3-methylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2- yclo-hexyloxy-4- [N-methyl- (3-methylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-methoxy-4- [N-methyl- (4-methylphenyl) amino]- 5- (trifluoromethyl) pyrimidine, 2-ethoxy-4- [N-methyl- (4-methylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-propoxy-4- [N-methyl -(4-methylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-iso-propoxy-4- [N-methyl- (4-methylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-butoxy-4- [N-methyl- (4-methylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-iso-butoxy- 4- [N-methyl- (4-methylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-sec-butoxy-4- [N-methyl- (4-methylphenyl) amino] -5- ( Trifluoromethyl) pyrimidine, 2-tert-butoxy-4- [N-methyl- (4-methylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-pentoxy-4- [N-methyl- (4-Methylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-cyclo-pentoxy-4- [N-methyl- (4-methylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2 -N-hexyloxy-4- [N-methyl- (4-methylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-cyclo-hex Aryloxy-4-[N-methyl - (4-methylphenyl) amino] -5- (trifluoromethyl) pyrimidine, and the like.
本発明の一般式(1)で表わされる2−アルコキシ−5−(トリフルオロメチル)ピリミジン誘導体でR1がエチル基である化合物としては、具体的には例えば、2−メトキシ−4−[N−メチル−(2−エチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−エトキシ−4−[N−メチル−(2−エチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−プロポキシ−4−[N−メチル−(2−エチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−iso−プロポキシ−4−[N−メチル−(2−エチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ブトキシ−4−[N−メチル−(2−エチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−iso−ブトキシ−4−[N−メチル−(2−エチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−sec−ブトキシ−4−[N−メチル−(2−エチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−tert−ブトキシ−4−[N−メチル−(2−エチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ペントキシ−4−[N−メチル−(2−エチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−cyclo−ペントキシ−4−[N−メチル−(2−エチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ヘキシルオキシ−4−[N−メチル−(2−エチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−cyclo−ヘキシルオキシ−4−[N−メチル−(2−エチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−メトキシ−4−[N−メチル−(3−エチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−エトキシ−4−[N−メチル−(3−エチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−プロポキシ−4−[N−メチル−(3−エチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−iso−プロポキシ−4−[N−メチル−(3−エチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ブトキシ−4−[N−メチル−(3−エチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−iso−ブトキシ−4−[N−メチル−(3−エチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−sec−ブトキシ−4−[N−メチル−(3−エチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−tert−ブトキシ−4−[N−メチル−(3−エチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ペントキシ−4−[N−メチル−(3−エチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−cyclo−ペントキシ−4−[N−メチル−(3−エチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ヘキシルオキシ−4−[N−メチル−(3−エチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−cyclo−ヘキシルオキシ−4−[N−メチル−(3−エチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−メトキシ−4−[N−メチル−(4−エチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−エトキシ−4−[N−メチル−(4−エチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−プロポキシ−4−[N−メチル−(4−エチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−iso−プロポキシ−4−[N−メチル−(4−エチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ブトキシ−4−[N−メチル−(4−エチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−iso−ブトキシ−4−[N−メチル−(4−エチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−sec−ブトキシ−4−[N−メチル−(4−エチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−tert−ブトキシ−4−[N−メチル−(4−エチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ペントキシ−4−[N−メチル−(4−エチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−cyclo−ペントキシ−4−[N−メチル−(4−エチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ヘキシルオキシ−4−[N−メチル−(4−エチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−cyclo−ヘキシルオキシ−4−[N−メチル−(4−エチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン等が挙げられる。 Specific examples of the 2-alkoxy-5- (trifluoromethyl) pyrimidine derivative represented by the general formula (1) of the present invention in which R 1 is an ethyl group include 2-methoxy-4- [N -Methyl- (2-ethylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-ethoxy-4- [N-methyl- (2-ethylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-propoxy-4- [N-methyl- (2-ethylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-iso-propoxy-4- [N-methyl- (2-ethylphenyl) Amino] -5- (trifluoromethyl) pyrimidine, 2-n-butoxy-4- [N-methyl- (2-ethylphenyl) amino] -5- (trifluoromethyl) pi Midine, 2-iso-butoxy-4- [N-methyl- (2-ethylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-sec-butoxy-4- [N-methyl- (2-ethyl) Phenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-tert-butoxy-4- [N-methyl- (2-ethylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-pentoxy -4- [N-methyl- (2-ethylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-cyclo-pentoxy-4- [N-methyl- (2-ethylphenyl) amino] -5 (Trifluoromethyl) pyrimidine, 2-n-hexyloxy-4- [N-methyl- (2-ethylphenyl) amino] -5- (trifluoromethyl) pi Limidine, 2-cyclo-hexyloxy-4- [N-methyl- (2-ethylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-methoxy-4- [N-methyl- (3-ethylphenyl) ) Amino] -5- (trifluoromethyl) pyrimidine, 2-ethoxy-4- [N-methyl- (3-ethylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-propoxy-4- [N-methyl- (3-ethylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-iso-propoxy-4- [N-methyl- (3-ethylphenyl) amino] -5- (trifluoro Methyl) pyrimidine, 2-n-butoxy-4- [N-methyl- (3-ethylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-i o-butoxy-4- [N-methyl- (3-ethylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-sec-butoxy-4- [N-methyl- (3-ethylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-tert-butoxy-4- [N-methyl- (3-ethylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-pentoxy-4- [ N-methyl- (3-ethylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-cyclo-pentoxy-4- [N-methyl- (3-ethylphenyl) amino] -5- (trifluoromethyl ) Pyrimidine, 2-n-hexyloxy-4- [N-methyl- (3-ethylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2- yclo-hexyloxy-4- [N-methyl- (3-ethylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-methoxy-4- [N-methyl- (4-ethylphenyl) amino]- 5- (trifluoromethyl) pyrimidine, 2-ethoxy-4- [N-methyl- (4-ethylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-propoxy-4- [N-methyl -(4-ethylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-iso-propoxy-4- [N-methyl- (4-ethylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-butoxy-4- [N-methyl- (4-ethylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-iso-butoxy- 4- [N-methyl- (4-ethylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-sec-butoxy-4- [N-methyl- (4-ethylphenyl) amino] -5- ( Trifluoromethyl) pyrimidine, 2-tert-butoxy-4- [N-methyl- (4-ethylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-pentoxy-4- [N-methyl- (4-Ethylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-cyclo-pentoxy-4- [N-methyl- (4-ethylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2 -N-hexyloxy-4- [N-methyl- (4-ethylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-cyclo-hex Aryloxy-4-[N-methyl - (4-ethylphenyl) amino] -5- (trifluoromethyl) pyrimidine, and the like.
本発明の一般式(1)で表わされる2−アルコキシ−5−(トリフルオロメチル)ピリミジン誘導体でR1がn−プロピル基である化合物としては、具体的には例えば、2−メトキシ−4−[N−メチル−(2−n−プロピルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−エトキシ−4−[N−メチル−(2−n−プロピルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−プロポキシ−4−[N−メチル−(2−n−プロピルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−iso−プロポキシ−4−[N−メチル−(2−n−プロピルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ブトキシ−4−[N−メチル−(2−n−プロピルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−iso−ブトキシ−4−[N−メチル−(2−n−プロピルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−sec−ブトキシ−4−[N−メチル−(2−n−プロピルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−tert−ブトキシ−4−[N−メチル−(2−n−プロピルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ペントキシ−4−[N−メチル−(2−n−プロピルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−cyclo−ペントキシ−4−[N−メチル−(2−n−プロピルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ヘキシルオキシ−4−[N−メチル−(2−n−プロピルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−cyclo−ヘキシルオキシ−4−[N−メチル−(2−n−プロピルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−メトキシ−4−[N−メチル−(3−n−プロピルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−エトキシ−4−[N−メチル−(3−n−プロピルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−プロポキシ−4−[N−メチル−(3−n−プロピルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−iso−プロポキシ−4−[N−メチル−(3−n−プロピルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ブトキシ−4−[N−メチル−(3−n−プロピルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−iso−ブトキシ−4−[N−メチル−(3−n−プロピルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−sec−ブトキシ−4−[N−メチル−(3−n−プロピルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−tert−ブトキシ−4−[N−メチル−(3−n−プロピルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ペントキシ−4−[N−メチル−(3−n−プロピルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−cyclo−ペントキシ−4−[N−メチル−(3−n−プロピルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ヘキシルオキシ−4−[N−メチル−(3−n−プロピルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−cyclo−ヘキシルオキシ−4−[N−メチル−(3−n−プロピルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−メトキシ−4−[N−メチル−(4−n−プロピルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−エトキシ−4−[N−メチル−(4−n−プロピルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−プロポキシ−4−[N−メチル−(4−n−プロピルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−iso−プロポキシ−4−[N−メチル−(4−n−プロピルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ブトキシ−4−[N−メチル−(4−n−プロピルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−iso−ブトキシ−4−[N−メチル−(4−n−プロピルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−sec−ブトキシ−4−[N−メチル−(4−n−プロピルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−tert−ブトキシ−4−[N−メチル−(4−n−プロピルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ペントキシ−4−[N−メチル−(4−n−プロピルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−cyclo−ペントキシ−4−[N−メチル−(4−n−プロピルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ヘキシルオキシ−4−[N−メチル−(4−n−プロピルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−cyclo−ヘキシルオキシ−4−[N−メチル−(4−n−プロピルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン等が挙げられる。 Specific examples of the 2-alkoxy-5- (trifluoromethyl) pyrimidine derivative represented by the general formula (1) of the present invention in which R 1 is an n-propyl group include 2-methoxy-4- [N-methyl- (2-n-propylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-ethoxy-4- [N-methyl- (2-n-propylphenyl) amino] -5- ( Trifluoromethyl) pyrimidine, 2-n-propoxy-4- [N-methyl- (2-n-propylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-iso-propoxy-4- [N- Methyl- (2-n-propylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-butoxy-4- [N-methyl- (2-n-propylphenyl) a No] -5- (trifluoromethyl) pyrimidine, 2-iso-butoxy-4- [N-methyl- (2-n-propylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-sec-butoxy -4- [N-methyl- (2-n-propylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-tert-butoxy-4- [N-methyl- (2-n-propylphenyl) amino ] -5- (trifluoromethyl) pyrimidine, 2-n-pentoxy-4- [N-methyl- (2-n-propylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-cyclo-pentoxy- 4- [N-methyl- (2-n-propylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-hexyloxy-4- [N-me Tyl- (2-n-propylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-cyclo-hexyloxy-4- [N-methyl- (2-n-propylphenyl) amino] -5- ( Trifluoromethyl) pyrimidine, 2-methoxy-4- [N-methyl- (3-n-propylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-ethoxy-4- [N-methyl- (3 -N-propylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-propoxy-4- [N-methyl- (3-n-propylphenyl) amino] -5- (trifluoromethyl) pyrimidine 2-iso-propoxy-4- [N-methyl- (3-n-propylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-butyl Xyl-4- [N-methyl- (3-n-propylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-iso-butoxy-4- [N-methyl- (3-n-propylphenyl) Amino] -5- (trifluoromethyl) pyrimidine, 2-sec-butoxy-4- [N-methyl- (3-n-propylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-tert-butoxy -4- [N-methyl- (3-n-propylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-pentoxy-4- [N-methyl- (3-n-propylphenyl) amino ] -5- (trifluoromethyl) pyrimidine, 2-cyclo-pentoxy-4- [N-methyl- (3-n-propylphenyl) amino] -5- (trifluoro Methyl) pyrimidine, 2-n-hexyloxy-4- [N-methyl- (3-n-propylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-cyclo-hexyloxy-4- [N- Methyl- (3-n-propylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-methoxy-4- [N-methyl- (4-n-propylphenyl) amino] -5- (trifluoromethyl) ) Pyrimidine, 2-ethoxy-4- [N-methyl- (4-n-propylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-propoxy-4- [N-methyl- (4- n-propylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-iso-propoxy-4- [N-methyl- (4-n-propylphenyl) a Mino] -5- (trifluoromethyl) pyrimidine, 2-n-butoxy-4- [N-methyl- (4-n-propylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-iso-butoxy -4- [N-methyl- (4-n-propylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-sec-butoxy-4- [N-methyl- (4-n-propylphenyl) amino ] -5- (trifluoromethyl) pyrimidine, 2-tert-butoxy-4- [N-methyl- (4-n-propylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-pentoxy- 4- [N-methyl- (4-n-propylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-cyclo-pentoxy-4- [N-methyl (4-n-propylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-hexyloxy-4- [N-methyl- (4-n-propylphenyl) amino] -5- (trifluoro Methyl) pyrimidine, 2-cyclo-hexyloxy-4- [N-methyl- (4-n-propylphenyl) amino] -5- (trifluoromethyl) pyrimidine, and the like.
本発明の一般式(1)で表わされる2−アルコキシ−5−(トリフルオロメチル)ピリミジン誘導体でR1がiso−プロピル基である化合物としては、具体的には例えば、2−メトキシ−4−[N−メチル−(2−iso−プロピルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−エトキシ−4−[N−メチル−(2−iso−プロピルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−プロポキシ−4−[N−メチル−(2−iso−プロピルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−iso−プロポキシ−4−[N−メチル−(2−iso−プロピルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ブトキシ−4−[N−メチル−(2−iso−プロピルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−iso−ブトキシ−4−[N−メチル−(2−iso−プロピルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−sec−ブトキシ−4−[N−メチル−(2−iso−プロピルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−tert−ブトキシ−4−[N−メチル−(2−iso−プロピルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ペントキシ−4−[N−メチル−(2−iso−プロピルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−cyclo−ペントキシ−4−[N−メチル−(2−iso−プロピルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ヘキシルオキシ−4−[N−メチル−(2−iso−プロピルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−cyclo−ヘキシルオキシ−4−[N−メチル−(2−iso−プロピルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−メトキシ−4−[N−メチル−(3−iso−プロピルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−エトキシ−4−[N−メチル−(3−iso−プロピルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−プロポキシ−4−[N−メチル−(3−iso−プロピルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−iso−プロポキシ−4−[N−メチル−(3−iso−プロピルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ブトキシ−4−[N−メチル−(3−iso−プロピルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−iso−ブトキシ−4−[N−メチル−(3−iso−プロピルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−sec−ブトキシ−4−[N−メチル−(3−iso−プロピルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−tert−ブトキシ−4−[N−メチル−(3−iso−プロピルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ペントキシ−4−[N−メチル−(3−iso−プロピルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−cyclo−ペントキシ−4−[N−メチル−(3−iso−プロピルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ヘキシルオキシ−4−[N−メチル−(3−iso−プロピルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−cyclo−ヘキシルオキシ−4−[N−メチル−(3−iso−プロピルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−メトキシ−4−[N−メチル−(4−iso−プロピルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−エトキシ−4−[N−メチル−(4−iso−プロピルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−プロポキシ−4−[N−メチル−(4−iso−プロピルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−iso−プロポキシ−4−[N−メチル−(4−iso−プロピルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ブトキシ−4−[N−メチル−(4−iso−プロピルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−iso−ブトキシ−4−[N−メチル−(4−iso−プロピルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−sec−ブトキシ−4−[N−メチル−(4−iso−プロピルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−tert−ブトキシ−4−[N−メチル−(4−iso−プロピルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ペントキシ−4−[N−メチル−(4−iso−プロピルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−cyclo−ペントキシ−4−[N−メチル−(4−iso−プロピルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ヘキシルオキシ−4−[N−メチル−(4−iso−プロピルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−cyclo−ヘキシルオキシ−4−[N−メチル−(4−iso−プロピルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン等が挙げられる。 Specific examples of the 2-alkoxy-5- (trifluoromethyl) pyrimidine derivative represented by the general formula (1) of the present invention in which R 1 is an iso-propyl group include 2-methoxy-4- [N-methyl- (2-iso-propylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-ethoxy-4- [N-methyl- (2-iso-propylphenyl) amino] -5- ( Trifluoromethyl) pyrimidine, 2-n-propoxy-4- [N-methyl- (2-iso-propylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-iso-propoxy-4- [N- Methyl- (2-iso-propylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-butoxy-4- [N-methyl- (2-is -Propylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-iso-butoxy-4- [N-methyl- (2-iso-propylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2 -Sec-butoxy-4- [N-methyl- (2-iso-propylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-tert-butoxy-4- [N-methyl- (2-iso- Propylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-pentoxy-4- [N-methyl- (2-iso-propylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2- cyclo-pentoxy-4- [N-methyl- (2-iso-propylphenyl) amino] -5- (trifluoromethyl) pyri Midine, 2-n-hexyloxy-4- [N-methyl- (2-iso-propylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-cyclo-hexyloxy-4- [N-methyl- (2-Iso-propylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-methoxy-4- [N-methyl- (3-iso-propylphenyl) amino] -5- (trifluoromethyl) pyrimidine 2-ethoxy-4- [N-methyl- (3-iso-propylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-propoxy-4- [N-methyl- (3-iso- Propylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-iso-propoxy-4- [N-methyl- (3-iso-propyl) Enyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-butoxy-4- [N-methyl- (3-iso-propylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-iso -Butoxy-4- [N-methyl- (3-iso-propylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-sec-butoxy-4- [N-methyl- (3-iso-propylphenyl) ) Amino] -5- (trifluoromethyl) pyrimidine, 2-tert-butoxy-4- [N-methyl- (3-iso-propylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n- Pentoxy-4- [N-methyl- (3-iso-propylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-cycl -Pentoxy-4- [N-methyl- (3-iso-propylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-hexyloxy-4- [N-methyl- (3-iso-propyl) Phenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-cyclo-hexyloxy-4- [N-methyl- (3-iso-propylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2- Methoxy-4- [N-methyl- (4-iso-propylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-ethoxy-4- [N-methyl- (4-iso-propylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-propoxy-4- [N-methyl- (4-iso-propylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-iso-propoxy-4- [N-methyl- (4-iso-propylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-butoxy-4 -[N-methyl- (4-iso-propylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-iso-butoxy-4- [N-methyl- (4-iso-propylphenyl) amino]- 5- (trifluoromethyl) pyrimidine, 2-sec-butoxy-4- [N-methyl- (4-iso-propylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-tert-butoxy-4- [N-methyl- (4-iso-propylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-pentoxy-4- [ -Methyl- (4-iso-propylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-cyclo-pentoxy-4- [N-methyl- (4-iso-propylphenyl) amino] -5- ( Trifluoromethyl) pyrimidine, 2-n-hexyloxy-4- [N-methyl- (4-iso-propylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-cyclo-hexyloxy-4- [ N-methyl- (4-iso-propylphenyl) amino] -5- (trifluoromethyl) pyrimidine and the like.
本発明の一般式(1)で表わされる2−アルコキシ−5−(トリフルオロメチル)ピリミジン誘導体でR1がn−ブチル基である化合物としては、具体的には例えば、2−メトキシ−4−[N−メチル−(2−n−ブチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−エトキシ−4−[N−メチル−(2−n−ブチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−プロポキシ−4−[N−メチル−(2−n−ブチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−iso−プロポキシ−4−[N−メチル−(2−n−ブチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ブトキシ−4−[N−メチル−(2−n−ブチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−iso−ブトキシ−4−[N−メチル−(2−n−ブチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−sec−ブトキシ−4−[N−メチル−(2−n−ブチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−tert−ブトキシ−4−[N−メチル−(2−n−ブチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ペントキシ−4−[N−メチル−(2−n−ブチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−cyclo−ペントキシ−4−[N−メチル−(2−n−ブチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ヘキシルオキシ−4−[N−メチル−(2−n−ブチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−cyclo−ヘキシルオキシ−4−[N−メチル−(2−n−ブチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−メトキシ−4−[N−メチル−(3−n−ブチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−エトキシ−4−[N−メチル−(3−n−ブチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−プロポキシ−4−[N−メチル−(3−n−ブチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−iso−プロポキシ−4−[N−メチル−(3−n−ブチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ブトキシ−4−[N−メチル−(3−n−ブチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−iso−ブトキシ−4−[N−メチル−(3−n−ブチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−sec−ブトキシ−4−[N−メチル−(3−n−ブチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−tert−ブトキシ−4−[N−メチル−(3−n−ブチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ペントキシ−4−[N−メチル−(3−n−ブチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−cyclo−ペントキシ−4−[N−メチル−(3−n−ブチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ヘキシルオキシ−4−[N−メチル−(3−n−ブチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−cyclo−ヘキシルオキシ−4−[N−メチル−(3−n−ブチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−メトキシ−4−[N−メチル−(4−n−ブチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−エトキシ−4−[N−メチル−(4−n−ブチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−プロポキシ−4−[N−メチル−(4−n−ブチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−iso−プロポキシ−4−[N−メチル−(4−n−ブチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ブトキシ−4−[N−メチル−(4−n−ブチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−iso−ブトキシ−4−[N−メチル−(4−n−ブチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−sec−ブトキシ−4−[N−メチル−(4−n−ブチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−tert−ブトキシ−4−[N−メチル−(4−n−ブチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ペントキシ−4−[N−メチル−(4−n−ブチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−cyclo−ペントキシ−4−[N−メチル−(4−n−ブチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ヘキシルオキシ−4−[N−メチル−(4−n−ブチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−cyclo−ヘキシルオキシ−4−[N−メチル−(4−n−ブチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン等が挙げられる。 Specific examples of the 2-alkoxy-5- (trifluoromethyl) pyrimidine derivative represented by the general formula (1) of the present invention in which R 1 is an n-butyl group include 2-methoxy-4- [N-methyl- (2-n-butylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-ethoxy-4- [N-methyl- (2-n-butylphenyl) amino] -5- ( Trifluoromethyl) pyrimidine, 2-n-propoxy-4- [N-methyl- (2-n-butylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-iso-propoxy-4- [N- Methyl- (2-n-butylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-butoxy-4- [N-methyl- (2-n-butylphenyl) amino] -5 Trifluoromethyl) pyrimidine, 2-iso-butoxy-4- [N-methyl- (2-n-butylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-sec-butoxy-4- [N- Methyl- (2-n-butylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-tert-butoxy-4- [N-methyl- (2-n-butylphenyl) amino] -5- (tri Fluoromethyl) pyrimidine, 2-n-pentoxy-4- [N-methyl- (2-n-butylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-cyclo-pentoxy-4- [N-methyl -(2-n-butylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-hexyloxy-4- [N-methyl- (2-n-butyl) Phenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-cyclo-hexyloxy-4- [N-methyl- (2-n-butylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2- Methoxy-4- [N-methyl- (3-n-butylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-ethoxy-4- [N-methyl- (3-n-butylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-propoxy-4- [N-methyl- (3-n-butylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-iso-propoxy-4 -[N-methyl- (3-n-butylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-butoxy-4- [N-methyl- (3-n Butylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-iso-butoxy-4- [N-methyl- (3-n-butylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2- sec-Butoxy-4- [N-methyl- (3-n-butylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-tert-butoxy-4- [N-methyl- (3-n-butyl) Phenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-pentoxy-4- [N-methyl- (3-n-butylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-cyclo -Pentoxy-4- [N-methyl- (3-n-butylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-hexyloxy- -[N-methyl- (3-n-butylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-cyclo-hexyloxy-4- [N-methyl- (3-n-butylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-methoxy-4- [N-methyl- (4-n-butylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-ethoxy-4- [N- Methyl- (4-n-butylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-propoxy-4- [N-methyl- (4-n-butylphenyl) amino] -5- (tri Fluoromethyl) pyrimidine, 2-iso-propoxy-4- [N-methyl- (4-n-butylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-but Xyl-4- [N-methyl- (4-n-butylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-iso-butoxy-4- [N-methyl- (4-n-butylphenyl) Amino] -5- (trifluoromethyl) pyrimidine, 2-sec-butoxy-4- [N-methyl- (4-n-butylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-tert-butoxy -4- [N-methyl- (4-n-butylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-pentoxy-4- [N-methyl- (4-n-butylphenyl) amino ] -5- (trifluoromethyl) pyrimidine, 2-cyclo-pentoxy-4- [N-methyl- (4-n-butylphenyl) amino] -5- (trifluoromethyl) pyri Gin, 2-n-hexyloxy-4- [N-methyl- (4-n-butylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-cyclo-hexyloxy-4- [N-methyl- (4-n-butylphenyl) amino] -5- (trifluoromethyl) pyrimidine and the like.
本発明の一般式(1)で表わされる2−アルコキシ−5−(トリフルオロメチル)ピリミジン誘導体でR1がiso−ブチル基である化合物としては、具体的には例えば、2−メトキシ−4−[N−メチル−(2−iso−ブチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−エトキシ−4−[N−メチル−(2−iso−ブチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−プロポキシ−4−[N−メチル−(2−iso−ブチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−iso−プロポキシ−4−[N−メチル−(2−iso−ブチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ブトキシ−4−[N−メチル−(2−iso−ブチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−iso−ブトキシ−4−[N−メチル−(2−iso−ブチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−sec−ブトキシ−4−[N−メチル−(2−iso−ブチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−tert−ブトキシ−4−[N−メチル−(2−iso−ブチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ペントキシ−4−[N−メチル−(2−iso−ブチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−cyclo−ペントキシ−4−[N−メチル−(2−iso−ブチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ヘキシルオキシ−4−[N−メチル−(2−iso−ブチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−cyclo−ヘキシルオキシ−4−[N−メチル−(2−iso−ブチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−メトキシ−4−[N−メチル−(3−iso−ブチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−エトキシ−4−[N−メチル−(3−iso−ブチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−プロポキシ−4−[N−メチル−(3−iso−ブチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−iso−プロポキシ−4−[N−メチル−(3−iso−ブチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ブトキシ−4−[N−メチル−(3−iso−ブチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−iso−ブトキシ−4−[N−メチル−(3−iso−ブチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−sec−ブトキシ−4−[N−メチル−(3−iso−ブチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−tert−ブトキシ−4−[N−メチル−(3−iso−ブチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ペントキシ−4−[N−メチル−(3−iso−ブチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−cyclo−ペントキシ−4−[N−メチル−(3−iso−ブチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ヘキシルオキシ−4−[N−メチル−(3−iso−ブチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−cyclo−ヘキシルオキシ−4−[N−メチル−(3−iso−ブチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−メトキシ−4−[N−メチル−(4−iso−ブチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−エトキシ−4−[N−メチル−(4−iso−ブチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−プロポキシ−4−[N−メチル−(4−iso−ブチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−iso−プロポキシ−4−[N−メチル−(4−iso−ブチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ブトキシ−4−[N−メチル−(4−iso−ブチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−iso−ブトキシ−4−[N−メチル−(4−iso−ブチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−sec−ブトキシ−4−[N−メチル−(4−iso−ブチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−tert−ブトキシ−4−[N−メチル−(4−iso−ブチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ペントキシ−4−[N−メチル−(4−iso−ブチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−cyclo−ペントキシ−4−[N−メチル−(4−iso−ブチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ヘキシルオキシ−4−[N−メチル−(4−iso−ブチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−cyclo−ヘキシルオキシ−4−[N−メチル−(4−iso−ブチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン等が挙げられる。 Specific examples of the 2-alkoxy-5- (trifluoromethyl) pyrimidine derivative represented by the general formula (1) of the present invention in which R 1 is an iso-butyl group include, for example, 2-methoxy-4- [N-methyl- (2-iso-butylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-ethoxy-4- [N-methyl- (2-iso-butylphenyl) amino] -5- ( Trifluoromethyl) pyrimidine, 2-n-propoxy-4- [N-methyl- (2-iso-butylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-iso-propoxy-4- [N- Methyl- (2-iso-butylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-butoxy-4- [N-methyl- (2-iso-butyl) Enyl) amino] -5- (trifluoromethyl) pyrimidine, 2-iso-butoxy-4- [N-methyl- (2-iso-butylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-sec -Butoxy-4- [N-methyl- (2-iso-butylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-tert-butoxy-4- [N-methyl- (2-iso-butylphenyl) ) Amino] -5- (trifluoromethyl) pyrimidine, 2-n-pentoxy-4- [N-methyl- (2-iso-butylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-cyclo- Pentoxy-4- [N-methyl- (2-iso-butylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-hexyl Ruoxy-4- [N-methyl- (2-iso-butylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-cyclo-hexyloxy-4- [N-methyl- (2-iso-butylphenyl) ) Amino] -5- (trifluoromethyl) pyrimidine, 2-methoxy-4- [N-methyl- (3-iso-butylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-ethoxy-4- [N-methyl- (3-iso-butylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-propoxy-4- [N-methyl- (3-iso-butylphenyl) amino] -5 -(Trifluoromethyl) pyrimidine, 2-iso-propoxy-4- [N-methyl- (3-iso-butylphenyl) amino] -5- (trifluoro Romethyl) pyrimidine, 2-n-butoxy-4- [N-methyl- (3-iso-butylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-iso-butoxy-4- [N-methyl- (3-Iso-butylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-sec-butoxy-4- [N-methyl- (3-iso-butylphenyl) amino] -5- (trifluoromethyl) ) Pyrimidine, 2-tert-butoxy-4- [N-methyl- (3-iso-butylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-pentoxy-4- [N-methyl- ( 3-iso-butylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-cyclo-pentoxy-4- [N-methyl- (3-is -Butylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-hexyloxy-4- [N-methyl- (3-iso-butylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-cyclo-hexyloxy-4- [N-methyl- (3-iso-butylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-methoxy-4- [N-methyl- (4-iso- Butylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-ethoxy-4- [N-methyl- (4-iso-butylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n- Propoxy-4- [N-methyl- (4-iso-butylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-iso-pro Poxy-4- [N-methyl- (4-iso-butylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-butoxy-4- [N-methyl- (4-iso-butylphenyl) Amino] -5- (trifluoromethyl) pyrimidine, 2-iso-butoxy-4- [N-methyl- (4-iso-butylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-sec-butoxy -4- [N-methyl- (4-iso-butylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-tert-butoxy-4- [N-methyl- (4-iso-butylphenyl) amino ] -5- (trifluoromethyl) pyrimidine, 2-n-pentoxy-4- [N-methyl- (4-iso-butylphenyl) amino] -5- (trifluoro) Romethyl) pyrimidine, 2-cyclo-pentoxy-4- [N-methyl- (4-iso-butylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-hexyloxy-4- [N-methyl -(4-Iso-butylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-cyclo-hexyloxy-4- [N-methyl- (4-iso-butylphenyl) amino] -5- (tri Fluoromethyl) pyrimidine and the like.
本発明の一般式(1)で表わされる2−アルコキシ−5−(トリフルオロメチル)ピリミジン誘導体でR1がsec−ブチル基である化合物としては、具体的には例えば、2−メトキシ−4−[N−メチル−(2−sec−ブチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−エトキシ−4−[N−メチル−(2−sec−ブチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−プロポキシ−4−[N−メチル−(2−sec−ブチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−iso−プロポキシ−4−[N−メチル−(2−sec−ブチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ブトキシ−4−[N−メチル−(2−sec−ブチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−iso−ブトキシ−4−[N−メチル−(2−sec−ブチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−sec−ブトキシ−4−[N−メチル−(2−sec−ブチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−tert−ブトキシ−4−[N−メチル−(2−sec−ブチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ペントキシ−4−[N−メチル−(2−sec−ブチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−cyclo−ペントキシ−4−[N−メチル−(2−sec−ブチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ヘキシルオキシ−4−[N−メチル−(2−sec−ブチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−cyclo−ヘキシルオキシ−4−[N−メチル−(2−sec−ブチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−メトキシ−4−[N−メチル−(3−sec−ブチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−エトキシ−4−[N−メチル−(3−sec−ブチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−プロポキシ−4−[N−メチル−(3−sec−ブチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−iso−プロポキシ−4−[N−メチル−(3−sec−ブチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ブトキシ−4−[N−メチル−(3−sec−ブチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−iso−ブトキシ−4−[N−メチル−(3−sec−ブチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−sec−ブトキシ−4−[N−メチル−(3−sec−ブチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−tert−ブトキシ−4−[N−メチル−(3−sec−ブチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ペントキシ−4−[N−メチル−(3−sec−ブチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−cyclo−ペントキシ−4−[N−メチル−(3−sec−ブチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ヘキシルオキシ−4−[N−メチル−(3−sec−ブチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−cyclo−ヘキシルオキシ−4−[N−メチル−(3−sec−ブチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−メトキシ−4−[N−メチル−(4−sec−ブチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−エトキシ−4−[N−メチル−(4−sec−ブチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−プロポキシ−4−[N−メチル−(4−sec−ブチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−iso−プロポキシ−4−[N−メチル−(4−sec−ブチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ブトキシ−4−[N−メチル−(4−sec−ブチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−iso−ブトキシ−4−[N−メチル−(4−sec−ブチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−sec−ブトキシ−4−[N−メチル−(4−sec−ブチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−tert−ブトキシ−4−[N−メチル−(4−sec−ブチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ペントキシ−4−[N−メチル−(4−sec−ブチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−cyclo−ペントキシ−4−[N−メチル−(4−sec−ブチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ヘキシルオキシ−4−[N−メチル−(4−sec−ブチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−cyclo−ヘキシルオキシ−4−[N−メチル−(4−sec−ブチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン等が挙げられる。 Specific examples of the 2-alkoxy-5- (trifluoromethyl) pyrimidine derivative represented by the general formula (1) of the present invention in which R 1 is a sec-butyl group include 2-methoxy-4- [N-methyl- (2-sec-butylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-ethoxy-4- [N-methyl- (2-sec-butylphenyl) amino] -5- ( Trifluoromethyl) pyrimidine, 2-n-propoxy-4- [N-methyl- (2-sec-butylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-iso-propoxy-4- [N- Methyl- (2-sec-butylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-butoxy-4- [N-methyl- (2-sec-butyl) Enyl) amino] -5- (trifluoromethyl) pyrimidine, 2-iso-butoxy-4- [N-methyl- (2-sec-butylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-sec -Butoxy-4- [N-methyl- (2-sec-butylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-tert-butoxy-4- [N-methyl- (2-sec-butylphenyl) ) Amino] -5- (trifluoromethyl) pyrimidine, 2-n-pentoxy-4- [N-methyl- (2-sec-butylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-cyclo- Pentoxy-4- [N-methyl- (2-sec-butylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-hexyl Ruoxy-4- [N-methyl- (2-sec-butylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-cyclo-hexyloxy-4- [N-methyl- (2-sec-butylphenyl) ) Amino] -5- (trifluoromethyl) pyrimidine, 2-methoxy-4- [N-methyl- (3-sec-butylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-ethoxy-4- [N-methyl- (3-sec-butylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-propoxy-4- [N-methyl- (3-sec-butylphenyl) amino] -5 -(Trifluoromethyl) pyrimidine, 2-iso-propoxy-4- [N-methyl- (3-sec-butylphenyl) amino] -5- (trifluoro Romethyl) pyrimidine, 2-n-butoxy-4- [N-methyl- (3-sec-butylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-iso-butoxy-4- [N-methyl- (3-sec-butylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-sec-butoxy-4- [N-methyl- (3-sec-butylphenyl) amino] -5- (trifluoromethyl) ) Pyrimidine, 2-tert-butoxy-4- [N-methyl- (3-sec-butylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-pentoxy-4- [N-methyl- ( 3-sec-butylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-cyclo-pentoxy-4- [N-methyl- (3-se -Butylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-hexyloxy-4- [N-methyl- (3-sec-butylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-cyclo-hexyloxy-4- [N-methyl- (3-sec-butylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-methoxy-4- [N-methyl- (4-sec- Butylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-ethoxy-4- [N-methyl- (4-sec-butylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n- Propoxy-4- [N-methyl- (4-sec-butylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-iso-pro Poxy-4- [N-methyl- (4-sec-butylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-butoxy-4- [N-methyl- (4-sec-butylphenyl) Amino] -5- (trifluoromethyl) pyrimidine, 2-iso-butoxy-4- [N-methyl- (4-sec-butylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-sec-butoxy -4- [N-methyl- (4-sec-butylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-tert-butoxy-4- [N-methyl- (4-sec-butylphenyl) amino ] -5- (trifluoromethyl) pyrimidine, 2-n-pentoxy-4- [N-methyl- (4-sec-butylphenyl) amino] -5- (trifluoro) (Romethyl) pyrimidine, 2-cyclo-pentoxy-4- [N-methyl- (4-sec-butylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-hexyloxy-4- [N-methyl -(4-sec-butylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-cyclo-hexyloxy-4- [N-methyl- (4-sec-butylphenyl) amino] -5- (tri Fluoromethyl) pyrimidine and the like.
本発明の一般式(1)で表わされる2−アルコキシ−5−(トリフルオロメチル)ピリミジン誘導体でR1がtert−ブチル基である化合物としては、具体的には例えば、2−メトキシ−4−[N−メチル−(2−tert−ブチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−エトキシ−4−[N−メチル−(2−tert−ブチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−プロポキシ−4−[N−メチル−(2−tert−ブチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−iso−プロポキシ−4−[N−メチル−(2−tert−ブチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ブトキシ−4−[N−メチル−(2−tert−ブチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−iso−ブトキシ−4−[N−メチル−(2−tert−ブチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−sec−ブトキシ−4−[N−メチル−(2−tert−ブチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−tert−ブトキシ−4−[N−メチル−(2−tert−ブチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ペントキシ−4−[N−メチル−(2−tert−ブチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−cyclo−ペントキシ−4−[N−メチル−(2−tert−ブチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ヘキシルオキシ−4−[N−メチル−(2−tert−ブチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−cyclo−ヘキシルオキシ−4−[N−メチル−(2−tert−ブチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−メトキシ−4−[N−メチル−(3−tert−ブチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−エトキシ−4−[N−メチル−(3−tert−ブチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−プロポキシ−4−[N−メチル−(3−tert−ブチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−iso−プロポキシ−4−[N−メチル−(3−tert−ブチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ブトキシ−4−[N−メチル−(3−tert−ブチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−iso−ブトキシ−4−[N−メチル−(3−tert−ブチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−sec−ブトキシ−4−[N−メチル−(3−tert−ブチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−tert−ブトキシ−4−[N−メチル−(3−tert−ブチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ペントキシ−4−[N−メチル−(3−tert−ブチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−cyclo−ペントキシ−4−[N−メチル−(3−tert−ブチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ヘキシルオキシ−4−[N−メチル−(3−tert−ブチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−cyclo−ヘキシルオキシ−4−[N−メチル−(3−tert−ブチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−メトキシ−4−[N−メチル−(4−tert−ブチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−エトキシ−4−[N−メチル−(4−tert−ブチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−プロポキシ−4−[N−メチル−(4−tert−ブチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−iso−プロポキシ−4−[N−メチル−(4−tert−ブチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ブトキシ−4−[N−メチル−(4−tert−ブチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−iso−ブトキシ−4−[N−メチル−(4−tert−ブチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−sec−ブトキシ−4−[N−メチル−(4−tert−ブチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−tert−ブトキシ−4−[N−メチル−(4−tert−ブチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ペントキシ−4−[N−メチル−(4−tert−ブチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−cyclo−ペントキシ−4−[N−メチル−(4−tert−ブチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ヘキシルオキシ−4−[N−メチル−(4−tert−ブチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−cyclo−ヘキシルオキシ−4−[N−メチル−(4−tert−ブチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン等が挙げられる。 Specific examples of the 2-alkoxy-5- (trifluoromethyl) pyrimidine derivative represented by the general formula (1) of the present invention in which R 1 is a tert-butyl group include 2-methoxy-4- [N-methyl- (2-tert-butylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-ethoxy-4- [N-methyl- (2-tert-butylphenyl) amino] -5- ( Trifluoromethyl) pyrimidine, 2-n-propoxy-4- [N-methyl- (2-tert-butylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-iso-propoxy-4- [N- Methyl- (2-tert-butylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-butoxy-4- [N-methyl- (2-te t-butylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-iso-butoxy-4- [N-methyl- (2-tert-butylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-sec-butoxy-4- [N-methyl- (2-tert-butylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-tert-butoxy-4- [N-methyl- (2-tert -Butylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-pentoxy-4- [N-methyl- (2-tert-butylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2 -Cyclo-pentoxy-4- [N-methyl- (2-tert-butylphenyl) amino] -5- (trifluoromethyl) pyri Midine, 2-n-hexyloxy-4- [N-methyl- (2-tert-butylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-cyclo-hexyloxy-4- [N-methyl- (2-tert-Butylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-methoxy-4- [N-methyl- (3-tert-butylphenyl) amino] -5- (trifluoromethyl) pyrimidine 2-ethoxy-4- [N-methyl- (3-tert-butylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-propoxy-4- [N-methyl- (3-tert- Butylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-iso-propoxy-4- [N-methyl- (3-tert-butyl) Enyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-butoxy-4- [N-methyl- (3-tert-butylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-iso -Butoxy-4- [N-methyl- (3-tert-butylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-sec-butoxy-4- [N-methyl- (3-tert-butylphenyl) ) Amino] -5- (trifluoromethyl) pyrimidine, 2-tert-butoxy-4- [N-methyl- (3-tert-butylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n- Pentoxy-4- [N-methyl- (3-tert-butylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-cycl -Pentoxy-4- [N-methyl- (3-tert-butylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-hexyloxy-4- [N-methyl- (3-tert-butyl) Phenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-cyclo-hexyloxy-4- [N-methyl- (3-tert-butylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2- Methoxy-4- [N-methyl- (4-tert-butylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-ethoxy-4- [N-methyl- (4-tert-butylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-propoxy-4- [N-methyl- (4-tert-butylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-iso-propoxy-4- [N-methyl- (4-tert-butylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-butoxy-4 -[N-methyl- (4-tert-butylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-iso-butoxy-4- [N-methyl- (4-tert-butylphenyl) amino]- 5- (trifluoromethyl) pyrimidine, 2-sec-butoxy-4- [N-methyl- (4-tert-butylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-tert-butoxy-4- [N-methyl- (4-tert-butylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-pentoxy-4- [ -Methyl- (4-tert-butylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-cyclo-pentoxy-4- [N-methyl- (4-tert-butylphenyl) amino] -5- ( Trifluoromethyl) pyrimidine, 2-n-hexyloxy-4- [N-methyl- (4-tert-butylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-cyclo-hexyloxy-4- [ N-methyl- (4-tert-butylphenyl) amino] -5- (trifluoromethyl) pyrimidine and the like.
本発明の一般式(1)で表わされる2−アルコキシ−5−(トリフルオロメチル)ピリミジン誘導体でR1がn−ペンチル基である化合物としては、具体的には例えば、2−メトキシ−4−[N−メチル−(2−n−ペンチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−エトキシ−4−[N−メチル−(2−n−ペンチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−プロポキシ−4−[N−メチル−(2−n−ペンチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−iso−プロポキシ−4−[N−メチル−(2−n−ペンチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ブトキシ−4−[N−メチル−(2−n−ペンチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−iso−ブトキシ−4−[N−メチル−(2−n−ペンチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−sec−ブトキシ−4−[N−メチル−(2−n−ペンチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−tert−ブトキシ−4−[N−メチル−(2−n−ペンチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ペントキシ−4−[N−メチル−(2−n−ペンチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−cyclo−ペントキシ−4−[N−メチル−(2−n−ペンチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ヘキシルオキシ−4−[N−メチル−(2−n−ペンチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−cyclo−ヘキシルオキシ−4−[N−メチル−(2−n−ペンチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−メトキシ−4−[N−メチル−(3−n−ペンチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−エトキシ−4−[N−メチル−(3−n−ペンチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−プロポキシ−4−[N−メチル−(3−n−ペンチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−iso−プロポキシ−4−[N−メチル−(3−n−ペンチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ブトキシ−4−[N−メチル−(3−n−ペンチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−iso−ブトキシ−4−[N−メチル−(3−n−ペンチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−sec−ブトキシ−4−[N−メチル−(3−n−ペンチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−tert−ブトキシ−4−[N−メチル−(3−n−ペンチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ペントキシ−4−[N−メチル−(3−n−ペンチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−cyclo−ペントキシ−4−[N−メチル−(3−n−ペンチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ヘキシルオキシ−4−[N−メチル−(3−n−ペンチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−cyclo−ヘキシルオキシ−4−[N−メチル−(3−n−ペンチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−メトキシ−4−[N−メチル−(4−n−ペンチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−エトキシ−4−(4−n−ペンチルフェニルアミノ)−5−(トリフルオロメチル)ピリミジン、2−n−プロポキシ−4−[N−メチル−(4−n−ペンチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−iso−プロポキシ−4−[N−メチル−(4−n−ペンチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ブトキシ−4−[N−メチル−(4−n−ペンチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−iso−ブトキシ−4−[N−メチル−(4−n−ペンチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−sec−ブトキシ−4−[N−メチル−(4−n−ペンチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−tert−ブトキシ−4−[N−メチル−(4−n−ペンチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ペントキシ−4−[N−メチル−(4−n−ペンチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−cyclo−ペントキシ−4−[N−メチル−(4−n−ペンチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ヘキシルオキシ−4−[N−メチル−(4−n−ペンチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−cyclo−ヘキシルオキシ−4−[N−メチル−(4−n−ペンチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン等が挙げられる。 Specific examples of the 2-alkoxy-5- (trifluoromethyl) pyrimidine derivative represented by the general formula (1) of the present invention in which R 1 is an n-pentyl group include 2-methoxy-4- [N-methyl- (2-n-pentylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-ethoxy-4- [N-methyl- (2-n-pentylphenyl) amino] -5- ( Trifluoromethyl) pyrimidine, 2-n-propoxy-4- [N-methyl- (2-n-pentylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-iso-propoxy-4- [N- Methyl- (2-n-pentylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-butoxy-4- [N-methyl- (2-n-pentylphenyl) a No] -5- (trifluoromethyl) pyrimidine, 2-iso-butoxy-4- [N-methyl- (2-n-pentylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-sec-butoxy -4- [N-methyl- (2-n-pentylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-tert-butoxy-4- [N-methyl- (2-n-pentylphenyl) amino ] -5- (trifluoromethyl) pyrimidine, 2-n-pentoxy-4- [N-methyl- (2-n-pentylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-cyclo-pentoxy- 4- [N-methyl- (2-n-pentylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-hexyloxy-4- [N-mes Tyl- (2-n-pentylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-cyclo-hexyloxy-4- [N-methyl- (2-n-pentylphenyl) amino] -5- ( Trifluoromethyl) pyrimidine, 2-methoxy-4- [N-methyl- (3-n-pentylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-ethoxy-4- [N-methyl- (3 -N-pentylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-propoxy-4- [N-methyl- (3-n-pentylphenyl) amino] -5- (trifluoromethyl) pyrimidine 2-iso-propoxy-4- [N-methyl- (3-n-pentylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-butyl Xyl-4- [N-methyl- (3-n-pentylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-iso-butoxy-4- [N-methyl- (3-n-pentylphenyl) Amino] -5- (trifluoromethyl) pyrimidine, 2-sec-butoxy-4- [N-methyl- (3-n-pentylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-tert-butoxy -4- [N-methyl- (3-n-pentylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-pentoxy-4- [N-methyl- (3-n-pentylphenyl) amino ] -5- (trifluoromethyl) pyrimidine, 2-cyclo-pentoxy-4- [N-methyl- (3-n-pentylphenyl) amino] -5- (trifluoro Methyl) pyrimidine, 2-n-hexyloxy-4- [N-methyl- (3-n-pentylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-cyclo-hexyloxy-4- [N- Methyl- (3-n-pentylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-methoxy-4- [N-methyl- (4-n-pentylphenyl) amino] -5- (trifluoromethyl) ) Pyrimidine, 2-ethoxy-4- (4-n-pentylphenylamino) -5- (trifluoromethyl) pyrimidine, 2-n-propoxy-4- [N-methyl- (4-n-pentylphenyl) amino ] -5- (trifluoromethyl) pyrimidine, 2-iso-propoxy-4- [N-methyl- (4-n-pentylphenyl) amino] -5- (to Trifluoromethyl) pyrimidine, 2-n-butoxy-4- [N-methyl- (4-n-pentylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-iso-butoxy-4- [N- Methyl- (4-n-pentylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-sec-butoxy-4- [N-methyl- (4-n-pentylphenyl) amino] -5- (tri Fluoromethyl) pyrimidine, 2-tert-butoxy-4- [N-methyl- (4-n-pentylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-pentoxy-4- [N-methyl -(4-n-pentylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-cyclo-pentoxy-4- [N-methyl- (4-n-pen) Ruphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-hexyloxy-4- [N-methyl- (4-n-pentylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2- and cyclo-hexyloxy-4- [N-methyl- (4-n-pentylphenyl) amino] -5- (trifluoromethyl) pyrimidine.
本発明の一般式(1)で表わされる2−アルコキシ−5−(トリフルオロメチル)ピリミジン誘導体でR1がcyclo−ペンチル基である化合物としては、具体的には例えば、2−メトキシ−4−[N−メチル−(2−cyclo−ペンチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−エトキシ−4−[N−メチル−(2−cyclo−ペンチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−プロポキシ−4−[N−メチル−(2−cyclo−ペンチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−iso−プロポキシ−4−[N−メチル−(2−cyclo−ペンチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ブトキシ−4−[N−メチル−(2−cyclo−ペンチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−iso−ブトキシ−4−[N−メチル−(2−cyclo−ペンチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−sec−ブトキシ−4−[N−メチル−(2−cyclo−ペンチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−tert−ブトキシ−4−[N−メチル−(2−cyclo−ペンチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ペントキシ−4−[N−メチル−(2−cyclo−ペンチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−cyclo−ペントキシ−4−[N−メチル−(2−cyclo−ペンチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ヘキシルオキシ−4−[N−メチル−(2−cyclo−ペンチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−cyclo−ヘキシルオキシ−4−[N−メチル−(2−cyclo−ペンチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−メトキシ−4−[N−メチル−(3−cyclo−ペンチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−エトキシ−4−[N−メチル−(3−cyclo−ペンチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−プロポキシ−4−[N−メチル−(3−cyclo−ペンチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−iso−プロポキシ−4−[N−メチル−(3−cyclo−ペンチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ブトキシ−4−[N−メチル−(3−cyclo−ペンチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−iso−ブトキシ−4−[N−メチル−(3−cyclo−ペンチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−sec−ブトキシ−4−[N−メチル−(3−cyclo−ペンチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−tert−ブトキシ−4−[N−メチル−(3−cyclo−ペンチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ペントキシ−4−[N−メチル−(3−cyclo−ペンチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−cyclo−ペントキシ−4−[N−メチル−(3−cyclo−ペンチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ヘキシルオキシ−4−[N−メチル−(3−cyclo−ペンチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−cyclo−ヘキシルオキシ−4−[N−メチル−(3−cyclo−ペンチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−メトキシ−4−[N−メチル−(4−cyclo−ペンチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−エトキシ−4−[N−メチル−(4−cyclo−ペンチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−プロポキシ−4−[N−メチル−(4−cyclo−ペンチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−iso−プロポキシ−4−[N−メチル−(4−cyclo−ペンチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ブトキシ−4−[N−メチル−(4−cyclo−ペンチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−iso−ブトキシ−4−[N−メチル−(4−cyclo−ペンチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−sec−ブトキシ−4−[N−メチル−(4−cyclo−ペンチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−tert−ブトキシ−4−[N−メチル−(4−cyclo−ペンチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ペントキシ−4−[N−メチル−(4−cyclo−ペンチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−cyclo−ペントキシ−4−[N−メチル−(4−cyclo−ペンチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ヘキシルオキシ−4−[N−メチル−(4−cyclo−ペンチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−cyclo−ヘキシルオキシ−4−[N−メチル−(4−cyclo−ペンチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン等が挙げられる。 Specific examples of the 2-alkoxy-5- (trifluoromethyl) pyrimidine derivative represented by the general formula (1) of the present invention in which R 1 is a cyclo-pentyl group include, for example, 2-methoxy-4- [N-methyl- (2-cyclo-pentylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-ethoxy-4- [N-methyl- (2-cyclo-pentylphenyl) amino] -5- ( Trifluoromethyl) pyrimidine, 2-n-propoxy-4- [N-methyl- (2-cyclo-pentylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-iso-propoxy-4- [N- Methyl- (2-cyclo-pentylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-butoxy-4- [N Methyl- (2-cyclo-pentylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-iso-butoxy-4- [N-methyl- (2-cyclo-pentylphenyl) amino] -5- (tri Fluoromethyl) pyrimidine, 2-sec-butoxy-4- [N-methyl- (2-cyclo-pentylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-tert-butoxy-4- [N-methyl -(2-cyclo-pentylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-pentoxy-4- [N-methyl- (2-cyclo-pentylphenyl) amino] -5- (trifluoro Methyl) pyrimidine, 2-cyclo-pentoxy-4- [N-methyl- (2-cyclo-pentylpheny) L) amino] -5- (trifluoromethyl) pyrimidine, 2-n-hexyloxy-4- [N-methyl- (2-cyclo-pentylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2- cyclo-hexyloxy-4- [N-methyl- (2-cyclo-pentylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-methoxy-4- [N-methyl- (3-cyclo-pentylphenyl) ) Amino] -5- (trifluoromethyl) pyrimidine, 2-ethoxy-4- [N-methyl- (3-cyclo-pentylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-propoxy- 4- [N-methyl- (3-cyclo-pentylphenyl) amino] -5- (trifluoromethyl) pyrimidine, -Iso-propoxy-4- [N-methyl- (3-cyclo-pentylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-butoxy-4- [N-methyl- (3-cyclo- Pentylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-iso-butoxy-4- [N-methyl- (3-cyclo-pentylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2- sec-Butoxy-4- [N-methyl- (3-cyclo-pentylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-tert-butoxy-4- [N-methyl- (3-cyclo-pentyl) Phenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-pentoxy-4- [N-methyl- (3-c) clo-pentylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-cyclo-pentoxy-4- [N-methyl- (3-cyclo-pentylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-hexyloxy-4- [N-methyl- (3-cyclo-pentylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-cyclo-hexyloxy-4- [N-methyl- (3 -Cyclo-pentylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-methoxy-4- [N-methyl- (4-cyclo-pentylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2 -Ethoxy-4- [N-methyl- (4-cyclo-pentylphenyl) amino] -5- (to (Rifluoromethyl) pyrimidine, 2-n-propoxy-4- [N-methyl- (4-cyclo-pentylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-iso-propoxy-4- [N- Methyl- (4-cyclo-pentylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-butoxy-4- [N-methyl- (4-cyclo-pentylphenyl) amino] -5- (tri Fluoromethyl) pyrimidine, 2-iso-butoxy-4- [N-methyl- (4-cyclo-pentylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-sec-butoxy-4- [N-methyl -(4-cyclo-pentylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-tert-butoxy -4- [N-methyl- (4-cyclo-pentylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-pentoxy-4- [N-methyl- (4-cyclo-pentylphenyl) amino ] -5- (trifluoromethyl) pyrimidine, 2-cyclo-pentoxy-4- [N-methyl- (4-cyclo-pentylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-hexyloxy -4- [N-methyl- (4-cyclo-pentylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-cyclo-hexyloxy-4- [N-methyl- (4-cyclo-pentylphenyl) Amino] -5- (trifluoromethyl) pyrimidine and the like.
本発明の一般式(1)で表わされる2−アルコキシ−5−(トリフルオロメチル)ピリミジン誘導体でR1がn−ヘキシル基である化合物としては、具体的には例えば、2−メトキシ−4−[N−メチル−(2−n−ヘキシルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−エトキシ−4−[N−メチル−(2−n−ヘキシルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−プロポキシ−4−[N−メチル−(2−n−ヘキシルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−iso−プロポキシ−4−[N−メチル−(2−n−ヘキシルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ブトキシ−4−[N−メチル−(2−n−ヘキシルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−iso−ブトキシ−4−[N−メチル−(2−n−ヘキシルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−sec−ブトキシ−4−[N−メチル−(2−n−ヘキシルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−tert−ブトキシ−4−[N−メチル−(2−n−ヘキシルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ペントキシ−4−[N−メチル−(2−n−ヘキシルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−cyclo−ペントキシ−4−[N−メチル−(2−n−ヘキシルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ヘキシルオキシ−4−[N−メチル−(2−n−ヘキシルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−cyclo−ヘキシルオキシ−4−[N−メチル−(2−n−ヘキシルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−メトキシ−4−[N−メチル−(3−n−ヘキシルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−エトキシ−4−[N−メチル−(3−n−ヘキシルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−プロポキシ−4−[N−メチル−(3−n−ヘキシルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−iso−プロポキシ−4−[N−メチル−(3−n−ヘキシルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ブトキシ−4−[N−メチル−(3−n−ヘキシルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−iso−ブトキシ−4−[N−メチル−(3−n−ヘキシルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−sec−ブトキシ−4−[N−メチル−(3−n−ヘキシルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−tert−ブトキシ−4−[N−メチル−(3−n−ヘキシルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ペントキシ−4−[N−メチル−(3−n−ヘキシルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−cyclo−ペントキシ−4−[N−メチル−(3−n−ヘキシルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ヘキシルオキシ−4−[N−メチル−(3−n−ヘキシルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−cyclo−ヘキシルオキシ−4−[N−メチル−(3−n−ヘキシルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−メトキシ−4−[N−メチル−(4−n−ヘキシルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−エトキシ−4−[N−メチル−(4−n−ヘキシルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−プロポキシ−4−[N−メチル−(4−n−ヘキシルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−iso−プロポキシ−4−[N−メチル−(4−n−ヘキシルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ブトキシ−4−[N−メチル−(4−n−ヘキシルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−iso−ブトキシ−4−[N−メチル−(4−n−ヘキシルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−sec−ブトキシ−4−[N−メチル−(4−n−ヘキシルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−tert−ブトキシ−4−[N−メチル−(4−n−ヘキシルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ペントキシ−4−[N−メチル−(4−n−ヘキシルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−cyclo−ペントキシ−4−[N−メチル−(4−n−ヘキシルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ヘキシルオキシ−4−[N−メチル−(4−n−ヘキシルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−cyclo−ヘキシルオキシ−4−[N−メチル−(4−n−ヘキシルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン等が挙げられる。 Specific examples of the 2-alkoxy-5- (trifluoromethyl) pyrimidine derivative represented by the general formula (1) of the present invention in which R 1 is an n-hexyl group include 2-methoxy-4- [N-methyl- (2-n-hexylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-ethoxy-4- [N-methyl- (2-n-hexylphenyl) amino] -5- ( Trifluoromethyl) pyrimidine, 2-n-propoxy-4- [N-methyl- (2-n-hexylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-iso-propoxy-4- [N- Methyl- (2-n-hexylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-butoxy-4- [N-methyl- (2-n-hexylphenyl) a No] -5- (trifluoromethyl) pyrimidine, 2-iso-butoxy-4- [N-methyl- (2-n-hexylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-sec-butoxy -4- [N-methyl- (2-n-hexylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-tert-butoxy-4- [N-methyl- (2-n-hexylphenyl) amino ] -5- (trifluoromethyl) pyrimidine, 2-n-pentoxy-4- [N-methyl- (2-n-hexylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-cyclo-pentoxy- 4- [N-methyl- (2-n-hexylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-hexyloxy-4- [N-mes Tyl- (2-n-hexylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-cyclo-hexyloxy-4- [N-methyl- (2-n-hexylphenyl) amino] -5- ( Trifluoromethyl) pyrimidine, 2-methoxy-4- [N-methyl- (3-n-hexylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-ethoxy-4- [N-methyl- (3 -N-hexylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-propoxy-4- [N-methyl- (3-n-hexylphenyl) amino] -5- (trifluoromethyl) pyrimidine 2-iso-propoxy-4- [N-methyl- (3-n-hexylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-butyl Xyl-4- [N-methyl- (3-n-hexylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-iso-butoxy-4- [N-methyl- (3-n-hexylphenyl) Amino] -5- (trifluoromethyl) pyrimidine, 2-sec-butoxy-4- [N-methyl- (3-n-hexylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-tert-butoxy -4- [N-methyl- (3-n-hexylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-pentoxy-4- [N-methyl- (3-n-hexylphenyl) amino ] -5- (trifluoromethyl) pyrimidine, 2-cyclo-pentoxy-4- [N-methyl- (3-n-hexylphenyl) amino] -5- (trifluoro Methyl) pyrimidine, 2-n-hexyloxy-4- [N-methyl- (3-n-hexylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-cyclo-hexyloxy-4- [N- Methyl- (3-n-hexylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-methoxy-4- [N-methyl- (4-n-hexylphenyl) amino] -5- (trifluoromethyl) ) Pyrimidine, 2-ethoxy-4- [N-methyl- (4-n-hexylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-propoxy-4- [N-methyl- (4- n-hexylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-iso-propoxy-4- [N-methyl- (4-n-hexylphenyl) a Mino] -5- (trifluoromethyl) pyrimidine, 2-n-butoxy-4- [N-methyl- (4-n-hexylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-iso-butoxy -4- [N-methyl- (4-n-hexylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-sec-butoxy-4- [N-methyl- (4-n-hexylphenyl) amino ] -5- (trifluoromethyl) pyrimidine, 2-tert-butoxy-4- [N-methyl- (4-n-hexylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-pentoxy- 4- [N-methyl- (4-n-hexylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-cyclo-pentoxy-4- [N-methyl (4-n-hexylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-hexyloxy-4- [N-methyl- (4-n-hexylphenyl) amino] -5- (trifluoro Methyl) pyrimidine, 2-cyclo-hexyloxy-4- [N-methyl- (4-n-hexylphenyl) amino] -5- (trifluoromethyl) pyrimidine, and the like.
本発明の一般式(1)で表わされる2−アルコキシ−5−(トリフルオロメチル)ピリミジン誘導体でR1がcyclo−ヘキシル基である化合物としては、具体的には例えば、2−メトキシ−4−[N−メチル−(2−cyclo−ヘキシルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−エトキシ−4−[N−メチル−(2−cyclo−ヘキシルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−プロポキシ−4−[N−メチル−(2−cyclo−ヘキシルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−iso−プロポキシ−4−[N−メチル−(2−cyclo−ヘキシルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ブトキシ−4−[N−メチル−(2−cyclo−ヘキシルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−iso−ブトキシ−4−[N−メチル−(2−cyclo−ヘキシルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−sec−ブトキシ−4−[N−メチル−(2−cyclo−ヘキシルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−tert−ブトキシ−4−[N−メチル−(2−cyclo−ヘキシルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ペントキシ−4−[N−メチル−(2−cyclo−ヘキシルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−cyclo−ペントキシ−4−[N−メチル−(2−cyclo−ヘキシルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ヘキシルオキシ−4−[N−メチル−(2−cyclo−ヘキシルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−cyclo−ヘキシルオキシ−4−[N−メチル−(2−cyclo−ヘキシルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−メトキシ−4−[N−メチル−(3−cyclo−ヘキシルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−エトキシ−4−[N−メチル−(3−cyclo−ヘキシルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−プロポキシ−4−[N−メチル−(3−cyclo−ヘキシルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−iso−プロポキシ−4−[N−メチル−(3−cyclo−ヘキシルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ブトキシ−4−[N−メチル−(3−cyclo−ヘキシルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−iso−ブトキシ−4−[N−メチル−(3−cyclo−ヘキシルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−sec−ブトキシ−4−[N−メチル−(3−cyclo−ヘキシルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−tert−ブトキシ−4−[N−メチル−(3−cyclo−ヘキシルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ペントキシ−4−[N−メチル−(3−cyclo−ヘキシルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−cyclo−ペントキシ−4−[N−メチル−(3−cyclo−ヘキシルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ヘキシルオキシ−4−[N−メチル−(3−cyclo−ヘキシルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−cyclo−ヘキシルオキシ−4−[N−メチル−(3−cyclo−ヘキシルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−メトキシ−4−[N−メチル−(4−cyclo−ヘキシルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−エトキシ−4−[N−メチル−(4−cyclo−ヘキシルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−プロポキシ−4−[N−メチル−(4−cyclo−ヘキシルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−iso−プロポキシ−4−[N−メチル−(4−cyclo−ヘキシルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ブトキシ−4−[N−メチル−(4−cyclo−ヘキシルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−iso−ブトキシ−4−[N−メチル−(4−cyclo−ヘキシルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−sec−ブトキシ−4−[N−メチル−(4−cyclo−ヘキシルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−tert−ブトキシ−4−[N−メチル−(4−cyclo−ヘキシルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ペントキシ−4−[N−メチル−(4−cyclo−ヘキシルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−cyclo−ペントキシ−4−[N−メチル−(4−cyclo−ヘキシルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ヘキシルオキシ−4−[N−メチル−(4−cyclo−ヘキシルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−cyclo−ヘキシルオキシ−4−[N−メチル−(4−cyclo−ヘキシルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン等が挙げられる。 Specific examples of the 2-alkoxy-5- (trifluoromethyl) pyrimidine derivative represented by the general formula (1) of the present invention in which R 1 is a cyclo-hexyl group include 2-methoxy-4- [N-methyl- (2-cyclo-hexylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-ethoxy-4- [N-methyl- (2-cyclo-hexylphenyl) amino] -5- ( Trifluoromethyl) pyrimidine, 2-n-propoxy-4- [N-methyl- (2-cyclo-hexylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-iso-propoxy-4- [N- Methyl- (2-cyclo-hexylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-butoxy-4- [N Methyl- (2-cyclo-hexylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-iso-butoxy-4- [N-methyl- (2-cyclo-hexylphenyl) amino] -5- (tri Fluoromethyl) pyrimidine, 2-sec-butoxy-4- [N-methyl- (2-cyclo-hexylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-tert-butoxy-4- [N-methyl -(2-cyclo-hexylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-pentoxy-4- [N-methyl- (2-cyclo-hexylphenyl) amino] -5- (trifluoro Methyl) pyrimidine, 2-cyclo-pentoxy-4- [N-methyl- (2-cyclo-hexylpheny) L) amino] -5- (trifluoromethyl) pyrimidine, 2-n-hexyloxy-4- [N-methyl- (2-cyclo-hexylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2- cyclo-hexyloxy-4- [N-methyl- (2-cyclo-hexylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-methoxy-4- [N-methyl- (3-cyclo-hexylphenyl) ) Amino] -5- (trifluoromethyl) pyrimidine, 2-ethoxy-4- [N-methyl- (3-cyclo-hexylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-propoxy- 4- [N-methyl- (3-cyclo-hexylphenyl) amino] -5- (trifluoromethyl) pyrimidine, -Iso-propoxy-4- [N-methyl- (3-cyclo-hexylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-butoxy-4- [N-methyl- (3-cyclo- Hexylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-iso-butoxy-4- [N-methyl- (3-cyclo-hexylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2- sec-Butoxy-4- [N-methyl- (3-cyclo-hexylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-tert-butoxy-4- [N-methyl- (3-cyclo-hexyl) Phenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-pentoxy-4- [N-methyl- (3-c) clo-hexylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-cyclo-pentoxy-4- [N-methyl- (3-cyclo-hexylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-hexyloxy-4- [N-methyl- (3-cyclo-hexylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-cyclo-hexyloxy-4- [N-methyl- (3 -Cyclo-hexylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-methoxy-4- [N-methyl- (4-cyclo-hexylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2 -Ethoxy-4- [N-methyl- (4-cyclo-hexylphenyl) amino] -5- (to Trifluoromethyl) pyrimidine, 2-n-propoxy-4- [N-methyl- (4-cyclo-hexylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-iso-propoxy-4- [N- Methyl- (4-cyclo-hexylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-butoxy-4- [N-methyl- (4-cyclyl-hexylphenyl) amino] -5- (tri Fluoromethyl) pyrimidine, 2-iso-butoxy-4- [N-methyl- (4-cyclo-hexylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-sec-butoxy-4- [N-methyl -(4-Cyclo-hexylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-tert-butoxy -4- [N-methyl- (4-cyclo-hexylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-pentoxy-4- [N-methyl- (4-cyclo-hexylphenyl) amino ] -5- (trifluoromethyl) pyrimidine, 2-cyclo-pentoxy-4- [N-methyl- (4-cyclo-hexylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-hexyloxy -4- [N-methyl- (4-cyclo-hexylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-cyclo-hexyloxy-4- [N-methyl- (4-cyclo-hexylphenyl) Amino] -5- (trifluoromethyl) pyrimidine and the like.
本発明の一般式(1)で表わされる2−アルコキシ−5−(トリフルオロメチル)ピリミジン誘導体でR1がメトキシ基である化合物としては、具体的には例えば、2−メトキシ−4−[N−メチル−(2−メトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−エトキシ−4−[N−メチル−(2−メトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−プロポキシ−4−[N−メチル−(2−メトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−iso−プロポキシ−4−[N−メチル−(2−メトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ブトキシ−4−[N−メチル−(2−メトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−iso−ブトキシ−4−[N−メチル−(2−メトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−sec−ブトキシ−4−[N−メチル−(2−メトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−tert−ブトキシ−4−[N−メチル−(2−メトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ペントキシ−4−[N−メチル−(2−メトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−cyclo−ペントキシ−4−[N−メチル−(2−メトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ヘキシルオキシ−4−[N−メチル−(2−メトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−cyclo−ヘキシルオキシ−4−[N−メチル−(2−メトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−メトキシ−4−[N−メチル−(3−メトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−エトキシ−4−[N−メチル−(3−メトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−プロポキシ−4−[N−メチル−(3−メトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−iso−プロポキシ−4−[N−メチル−(3−メトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ブトキシ−4−[N−メチル−(3−メトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−iso−ブトキシ−4−[N−メチル−(3−メトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−sec−ブトキシ−4−[N−メチル−(3−メトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−tert−ブトキシ−4−[N−メチル−(3−メトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ペントキシ−4−[N−メチル−(3−メトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−cyclo−ペントキシ−4−[N−メチル−(3−メトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ヘキシルオキシ−4−[N−メチル−(3−メトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−cyclo−ヘキシルオキシ−4−[N−メチル−(3−メトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−メトキシ−4−[N−メチル−(4−メトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−エトキシ−4−[N−メチル−(4−メトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−プロポキシ−4−[N−メチル−(4−メトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−iso−プロポキシ−4−[N−メチル−(4−メトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ブトキシ−4−[N−メチル−(4−メトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−iso−ブトキシ−4−[N−メチル−(4−メトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−sec−ブトキシ−4−[N−メチル−(4−メトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−tert−ブトキシ−4−[N−メチル−(4−メトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ペントキシ−4−[N−メチル−(4−メトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−cyclo−ペントキシ−4−[N−メチル−(4−メトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ヘキシルオキシ−4−[N−メチル−(4−メトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−cyclo−ヘキシルオキシ−4−[N−メチル−(4−メトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン等が挙げられる。 Specific examples of the 2-alkoxy-5- (trifluoromethyl) pyrimidine derivative represented by the general formula (1) of the present invention in which R 1 is a methoxy group include, for example, 2-methoxy-4- [N -Methyl- (2-methoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-ethoxy-4- [N-methyl- (2-methoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-propoxy-4- [N-methyl- (2-methoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-iso-propoxy-4- [N-methyl- (2-methoxyphenyl) Amino] -5- (trifluoromethyl) pyrimidine, 2-n-butoxy-4- [N-methyl- (2-methoxyphenyl) amino] -5- (trifluoro) Methyl) pyrimidine, 2-iso-butoxy-4- [N-methyl- (2-methoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-sec-butoxy-4- [N-methyl- (2 -Methoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-tert-butoxy-4- [N-methyl- (2-methoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n -Pentoxy-4- [N-methyl- (2-methoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-cyclo-pentoxy-4- [N-methyl- (2-methoxyphenyl) amino]- 5- (trifluoromethyl) pyrimidine, 2-n-hexyloxy-4- [N-methyl- (2-methoxyphenyl) amino] -5 (Trifluoromethyl) pyrimidine, 2-cyclo-hexyloxy-4- [N-methyl- (2-methoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-methoxy-4- [N-methyl- (3-methoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-ethoxy-4- [N-methyl- (3-methoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n -Propoxy-4- [N-methyl- (3-methoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-iso-propoxy-4- [N-methyl- (3-methoxyphenyl) amino]- 5- (trifluoromethyl) pyrimidine, 2-n-butoxy-4- [N-methyl- (3-methoxyphenyl) amino] -5- (to Fluoromethyl) pyrimidine, 2-iso-butoxy-4- [N-methyl- (3-methoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-sec-butoxy-4- [N-methyl- ( 3-methoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-tert-butoxy-4- [N-methyl- (3-methoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2- n-pentoxy-4- [N-methyl- (3-methoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-cyclo-pentoxy-4- [N-methyl- (3-methoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-hexyloxy-4- [N-methyl- (3-methoxyphenyl) ami ] -5- (trifluoromethyl) pyrimidine, 2-cyclo-hexyloxy-4- [N-methyl- (3-methoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-methoxy-4- [ N-methyl- (4-methoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-ethoxy-4- [N-methyl- (4-methoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine 2-n-propoxy-4- [N-methyl- (4-methoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-iso-propoxy-4- [N-methyl- (4-methoxyphenyl) ) Amino] -5- (trifluoromethyl) pyrimidine, 2-n-butoxy-4- [N-methyl- (4-methoxyphenyl) amino]- 5- (trifluoromethyl) pyrimidine, 2-iso-butoxy-4- [N-methyl- (4-methoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-sec-butoxy-4- [N -Methyl- (4-methoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-tert-butoxy-4- [N-methyl- (4-methoxyphenyl) amino] -5- (trifluoromethyl) Pyrimidine, 2-n-pentoxy-4- [N-methyl- (4-methoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-cyclo-pentoxy-4- [N-methyl- (4-methoxy) Phenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-hexyloxy-4- [N-methyl- (4-methoxypheny) ) Amino] -5- (trifluoromethyl) pyrimidine, 2-cyclo- hexyloxy-4-[N-methyl - (4-methoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, and the like.
本発明の一般式(1)で表わされる2−アルコキシ−5−(トリフルオロメチル)ピリミジン誘導体でR1がエトキシ基である化合物としては、具体的には例えば、2−メトキシ−4−[N−メチル−(2−エトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−エトキシ−4−[N−メチル−(2−エトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−プロポキシ−4−[N−メチル−(2−エトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−iso−プロポキシ−4−[N−メチル−(2−エトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ブトキシ−4−[N−メチル−(2−エトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−iso−ブトキシ−4−[N−メチル−(2−エトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−sec−ブトキシ−4−[N−メチル−(2−エトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−tert−ブトキシ−4−[N−メチル−(2−エトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ペントキシ−4−[N−メチル−(2−エトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−cyclo−ペントキシ−4−[N−メチル−(2−エトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ヘキシルオキシ−4−[N−メチル−(2−エトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−cyclo−ヘキシルオキシ−4−[N−メチル−(2−エトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−メトキシ−4−[N−メチル−(3−エトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−エトキシ−4−[N−メチル−(3−エトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−プロポキシ−4−[N−メチル−(3−エトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−iso−プロポキシ−4−[N−メチル−(3−エトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ブトキシ−4−[N−メチル−(3−エトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−iso−ブトキシ−4−[N−メチル−(3−エトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−sec−ブトキシ−4−[N−メチル−(3−エトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−tert−ブトキシ−4−[N−メチル−(3−エトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ペントキシ−4−[N−メチル−(3−エトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−cyclo−ペントキシ−4−[N−メチル−(3−エトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ヘキシルオキシ−4−[N−メチル−(3−エトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−cyclo−ヘキシルオキシ−4−[N−メチル−(3−エトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−メトキシ−4−[N−メチル−(4−エトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−エトキシ−4−[N−メチル−(4−エトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−プロポキシ−4−[N−メチル−(4−エトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−iso−プロポキシ−4−[N−メチル−(4−エトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ブトキシ−4−[N−メチル−(4−エトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−iso−ブトキシ−4−[N−メチル−(4−エトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−sec−ブトキシ−4−[N−メチル−(4−エトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−tert−ブトキシ−4−[N−メチル−(4−エトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ペントキシ−4−[N−メチル−(4−エトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−cyclo−ペントキシ−4−[N−メチル−(4−エトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ヘキシルオキシ−4−[N−メチル−(4−エトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−cyclo−ヘキシルオキシ−4−[N−メチル−(4−エトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン等が挙げられる。 Specific examples of the 2-alkoxy-5- (trifluoromethyl) pyrimidine derivative represented by the general formula (1) of the present invention in which R 1 is an ethoxy group include, for example, 2-methoxy-4- [N -Methyl- (2-ethoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-ethoxy-4- [N-methyl- (2-ethoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-propoxy-4- [N-methyl- (2-ethoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-iso-propoxy-4- [N-methyl- (2-ethoxyphenyl) Amino] -5- (trifluoromethyl) pyrimidine, 2-n-butoxy-4- [N-methyl- (2-ethoxyphenyl) amino] -5- (trifluoro Methyl) pyrimidine, 2-iso-butoxy-4- [N-methyl- (2-ethoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-sec-butoxy-4- [N-methyl- (2 -Ethoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-tert-butoxy-4- [N-methyl- (2-ethoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n -Pentoxy-4- [N-methyl- (2-ethoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-cyclo-pentoxy-4- [N-methyl- (2-ethoxyphenyl) amino]- 5- (trifluoromethyl) pyrimidine, 2-n-hexyloxy-4- [N-methyl- (2-ethoxyphenyl) amino] -5 (Trifluoromethyl) pyrimidine, 2-cyclo-hexyloxy-4- [N-methyl- (2-ethoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-methoxy-4- [N-methyl- (3-Ethoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-ethoxy-4- [N-methyl- (3-ethoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n -Propoxy-4- [N-methyl- (3-ethoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-iso-propoxy-4- [N-methyl- (3-ethoxyphenyl) amino]- 5- (trifluoromethyl) pyrimidine, 2-n-butoxy-4- [N-methyl- (3-ethoxyphenyl) amino] -5- (to Fluoromethyl) pyrimidine, 2-iso-butoxy-4- [N-methyl- (3-ethoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-sec-butoxy-4- [N-methyl- ( 3-ethoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-tert-butoxy-4- [N-methyl- (3-ethoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2- n-pentoxy-4- [N-methyl- (3-ethoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-cyclo-pentoxy-4- [N-methyl- (3-ethoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-hexyloxy-4- [N-methyl- (3-ethoxyphenyl) ami ] -5- (trifluoromethyl) pyrimidine, 2-cyclo-hexyloxy-4- [N-methyl- (3-ethoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-methoxy-4- [ N-methyl- (4-ethoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-ethoxy-4- [N-methyl- (4-ethoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine 2-n-propoxy-4- [N-methyl- (4-ethoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-iso-propoxy-4- [N-methyl- (4-ethoxyphenyl) ) Amino] -5- (trifluoromethyl) pyrimidine, 2-n-butoxy-4- [N-methyl- (4-ethoxyphenyl) amino]- 5- (trifluoromethyl) pyrimidine, 2-iso-butoxy-4- [N-methyl- (4-ethoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-sec-butoxy-4- [N -Methyl- (4-ethoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-tert-butoxy-4- [N-methyl- (4-ethoxyphenyl) amino] -5- (trifluoromethyl) Pyrimidine, 2-n-pentoxy-4- [N-methyl- (4-ethoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-cyclo-pentoxy-4- [N-methyl- (4-ethoxy) Phenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-hexyloxy-4- [N-methyl- (4-ethoxypheny) ) Amino] -5- (trifluoromethyl) pyrimidine, 2-cyclo- hexyloxy-4-[N-methyl - (4-ethoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, and the like.
本発明の一般式(1)で表わされる2−アルコキシ−5−(トリフルオロメチル)ピリミジン誘導体でR1がn−プロポキシ基である化合物としては、具体的には例えば、2−メトキシ−4−[N−メチル−(2−n−プロポキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−エトキシ−4−[N−メチル−(2−n−プロポキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−プロポキシ−4−[N−メチル−(2−n−プロポキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−プロポキシ−4−[N−メチル−(2−n−プロポキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−iso−プロポキシ−4−[N−メチル−(2−n−プロポキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ブトキシ−4−[N−メチル−(2−n−プロポキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−iso−ブトキシ−4−[N−メチル−(2−n−プロポキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−sec−ブトキシ−4−[N−メチル−(2−n−プロポキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−tert−ブトキシ−4−[N−メチル−(2−n−プロポキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ペントキシ−4−[N−メチル−(2−n−プロポキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−cyclo−ペントキシ−4−[N−メチル−(2−n−プロポキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ヘキシルオキシ−4−[N−メチル−(2−n−プロポキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−cyclo−ヘキシルオキシ−4−[N−メチル−(2−n−プロポキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−メトキシ−4−[N−メチル−(3−n−プロポキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−エトキシ−4−[N−メチル−(3−n−プロポキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−プロポキシ−4−[N−メチル−(3−n−プロポキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−プロポキシ−4−[N−メチル−(3−n−プロポキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−iso−プロポキシ−4−[N−メチル−(3−n−プロポキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ブトキシ−4−[N−メチル−(3−n−プロポキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−iso−ブトキシ−4−[N−メチル−(3−n−プロポキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−sec−ブトキシ−4−[N−メチル−(3−n−プロポキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−tert−ブトキシ−4−[N−メチル−(3−n−プロポキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ペントキシ−4−[N−メチル−(3−n−プロポキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−cyclo−ペントキシ−4−[N−メチル−(3−n−プロポキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ヘキシルオキシ−4−[N−メチル−(3−n−プロポキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−cyclo−ヘキシルオキシ−4−[N−メチル−(3−n−プロポキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−メトキシ−4−[N−メチル−(4−n−プロポキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−エトキシ−4−[N−メチル−(4−n−プロポキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−プロポキシ−4−[N−メチル−(4−n−プロポキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−プロポキシ−4−[N−メチル−(4−n−プロポキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−iso−プロポキシ−4−[N−メチル−(4−n−プロポキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ブトキシ−4−[N−メチル−(4−n−プロポキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−iso−ブトキシ−4−[N−メチル−(4−n−プロポキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−sec−ブトキシ−4−[N−メチル−(4−n−プロポキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−tert−ブトキシ−4−[N−メチル−(4−n−プロポキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ペントキシ−4−[N−メチル−(4−n−プロポキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−cyclo−ペントキシ−4−[N−メチル−(4−n−プロポキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ヘキシルオキシ−4−[N−メチル−(4−n−プロポキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−cyclo−ヘキシルオキシ−4−[N−メチル−(4−n−プロポキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン等が挙げられる。 Specific examples of the 2-alkoxy-5- (trifluoromethyl) pyrimidine derivative represented by the general formula (1) of the present invention in which R 1 is an n-propoxy group include 2-methoxy-4- [N-methyl- (2-n-propoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-ethoxy-4- [N-methyl- (2-n-propoxyphenyl) amino] -5- ( Trifluoromethyl) pyrimidine, 2-n-propoxy-4- [N-methyl- (2-n-propoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-propoxy-4- [N- Methyl- (2-n-propoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-iso-propoxy-4- [N-methyl- (2-n-propoxy) Phenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-butoxy-4- [N-methyl- (2-n-propoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-iso -Butoxy-4- [N-methyl- (2-n-propoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-sec-butoxy-4- [N-methyl- (2-n-propoxyphenyl) ) Amino] -5- (trifluoromethyl) pyrimidine, 2-tert-butoxy-4- [N-methyl- (2-n-propoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n- Pentoxy-4- [N-methyl- (2-n-propoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-cyclo-pent Xyl-4- [N-methyl- (2-n-propoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-hexyloxy-4- [N-methyl- (2-n-propoxyphenyl) ) Amino] -5- (trifluoromethyl) pyrimidine, 2-cyclo-hexyloxy-4- [N-methyl- (2-n-propoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-methoxy -4- [N-methyl- (3-n-propoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-ethoxy-4- [N-methyl- (3-n-propoxyphenyl) amino]- 5- (trifluoromethyl) pyrimidine, 2-n-propoxy-4- [N-methyl- (3-n-propoxyphenyl) amino] -5- (trifluoro Til) pyrimidine, 2-n-propoxy-4- [N-methyl- (3-n-propoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-iso-propoxy-4- [N-methyl- (3-n-propoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-butoxy-4- [N-methyl- (3-n-propoxyphenyl) amino] -5- (trifluoromethyl ) Pyrimidine, 2-iso-butoxy-4- [N-methyl- (3-n-propoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-sec-butoxy-4- [N-methyl- ( 3-n-propoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-tert-butoxy-4- [N-methyl- (3-n-propoxy) Phenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-pentoxy-4- [N-methyl- (3-n-propoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-cyclo -Pentoxy-4- [N-methyl- (3-n-propoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-hexyloxy-4- [N-methyl- (3-n-propoxy) Phenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-cyclo-hexyloxy-4- [N-methyl- (3-n-propoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2- Methoxy-4- [N-methyl- (4-n-propoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-ethoxy Ci-4- [N-methyl- (4-n-propoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-propoxy-4- [N-methyl- (4-n-propoxyphenyl) Amino] -5- (trifluoromethyl) pyrimidine, 2-n-propoxy-4- [N-methyl- (4-n-propoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-iso-propoxy -4- [N-methyl- (4-n-propoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-butoxy-4- [N-methyl- (4-n-propoxyphenyl) amino ] -5- (trifluoromethyl) pyrimidine, 2-iso-butoxy-4- [N-methyl- (4-n-propoxyphenyl) amino] -5- (trifluorome ) Pyrimidine, 2-sec-butoxy-4- [N-methyl- (4-n-propoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-tert-butoxy-4- [N-methyl- (4-n-propoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-pentoxy-4- [N-methyl- (4-n-propoxyphenyl) amino] -5- (trifluoromethyl ) Pyrimidine, 2-cyclo-pentoxy-4- [N-methyl- (4-n-propoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-hexyloxy-4- [N-methyl- (4-n-propoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-cyclo-hexyloxy-4- [N-methyl- 4-n-propoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, and the like.
本発明の一般式(1)で表わされる2−アルコキシ−5−(トリフルオロメチル)ピリミジン誘導体でR1がiso−プロポキシ基である化合物としては、具体的には例えば、2−メトキシ−4−[N−メチル−(2−iso−プロポキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−エトキシ−4−[N−メチル−(2−iso−プロポキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−プロポキシ−4−[N−メチル−(2−iso−プロポキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−プロポキシ−4−[N−メチル−(2−iso−プロポキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−iso−プロポキシ−4−[N−メチル−(2−iso−プロポキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ブトキシ−4−[N−メチル−(2−iso−プロポキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−iso−ブトキシ−4−[N−メチル−(2−iso−プロポキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−sec−ブトキシ−4−[N−メチル−(2−iso−プロポキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−tert−ブトキシ−4−[N−メチル−(2−iso−プロポキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ペントキシ−4−[N−メチル−(2−iso−プロポキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−cyclo−ペントキシ−4−[N−メチル−(2−iso−プロポキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ヘキシルオキシ−4−[N−メチル−(2−iso−プロポキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−cyclo−ヘキシルオキシ−4−[N−メチル−(2−iso−プロポキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−メトキシ−4−[N−メチル−(3−iso−プロポキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−エトキシ−4−[N−メチル−(3−iso−プロポキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−プロポキシ−4−[N−メチル−(3−iso−プロポキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−プロポキシ−4−[N−メチル−(3−iso−プロポキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−iso−プロポキシ−4−[N−メチル−(3−iso−プロポキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ブトキシ−4−[N−メチル−(3−iso−プロポキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−iso−ブトキシ−4−[N−メチル−(3−iso−プロポキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−sec−ブトキシ−4−[N−メチル−(3−iso−プロポキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−tert−ブトキシ−4−[N−メチル−(3−iso−プロポキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ペントキシ−4−[N−メチル−(3−iso−プロポキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−cyclo−ペントキシ−4−[N−メチル−(3−iso−プロポキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ヘキシルオキシ−4−[N−メチル−(3−iso−プロポキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−cyclo−ヘキシルオキシ−4−[N−メチル−(3−iso−プロポキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−メトキシ−4−[N−メチル−(4−iso−プロポキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−エトキシ−4−[N−メチル−(4−iso−プロポキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−プロポキシ−4−[N−メチル−(4−iso−プロポキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−プロポキシ−4−[N−メチル−(4−iso−プロポキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−iso−プロポキシ−4−[N−メチル−(4−iso−プロポキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ブトキシ−4−[N−メチル−(4−iso−プロポキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−iso−ブトキシ−4−[N−メチル−(4−iso−プロポキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−sec−ブトキシ−4−[N−メチル−(4−iso−プロポキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−tert−ブトキシ−4−[N−メチル−(4−iso−プロポキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ペントキシ−4−[N−メチル−(4−iso−プロポキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−cyclo−ペントキシ−4−[N−メチル−(4−iso−プロポキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ヘキシルオキシ−4−[N−メチル−(4−iso−プロポキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−cyclo−ヘキシルオキシ−4−[N−メチル−(4−iso−プロポキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン等が挙げられる。 Specific examples of the 2-alkoxy-5- (trifluoromethyl) pyrimidine derivative represented by the general formula (1) of the present invention in which R 1 is an iso-propoxy group include 2-methoxy-4- [N-methyl- (2-iso-propoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-ethoxy-4- [N-methyl- (2-iso-propoxyphenyl) amino] -5- ( Trifluoromethyl) pyrimidine, 2-n-propoxy-4- [N-methyl- (2-iso-propoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-propoxy-4- [N- Methyl- (2-iso-propoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-iso-propoxy-4- [N-methyl (2-Iso-propoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-butoxy-4- [N-methyl- (2-iso-propoxyphenyl) amino] -5- (trifluoromethyl) ) Pyrimidine, 2-iso-butoxy-4- [N-methyl- (2-iso-propoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-sec-butoxy-4- [N-methyl- ( 2-iso-propoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-tert-butoxy-4- [N-methyl- (2-iso-propoxyphenyl) amino] -5- (trifluoromethyl) Pyrimidine, 2-n-pentoxy-4- [N-methyl- (2-iso-propoxyphenyl) amino] -5- (trifluoro (Romethyl) pyrimidine, 2-cyclo-pentoxy-4- [N-methyl- (2-iso-propoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-hexyloxy-4- [N-methyl -(2-Iso-propoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-cyclo-hexyloxy-4- [N-methyl- (2-iso-propoxyphenyl) amino] -5- (tri Fluoromethyl) pyrimidine, 2-methoxy-4- [N-methyl- (3-iso-propoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-ethoxy-4- [N-methyl- (3- iso-propoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-propoxy-4- [N-me Ru- (3-iso-propoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-propoxy-4- [N-methyl- (3-iso-propoxyphenyl) amino] -5- (tri Fluoromethyl) pyrimidine, 2-iso-propoxy-4- [N-methyl- (3-iso-propoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-butoxy-4- [N-methyl -(3-Iso-propoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-iso-butoxy-4- [N-methyl- (3-iso-propoxyphenyl) amino] -5- (trifluoro Methyl) pyrimidine, 2-sec-butoxy-4- [N-methyl- (3-iso-propoxyphenyl) amino] -5- (tri Fluoromethyl) pyrimidine, 2-tert-butoxy-4- [N-methyl- (3-iso-propoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-pentoxy-4- [N-methyl- (3-Iso-propoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-cyclo-pentoxy-4- [N-methyl- (3-iso-propoxyphenyl) amino] -5- (trifluoromethyl) ) Pyrimidine, 2-n-hexyloxy-4- [N-methyl- (3-iso-propoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-cyclo-hexyloxy-4- [N-methyl] -(3-Iso-propoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-methoxy -4- [N-methyl- (4-iso-propoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-ethoxy-4- [N-methyl- (4-iso-propoxyphenyl) amino]- 5- (trifluoromethyl) pyrimidine, 2-n-propoxy-4- [N-methyl- (4-iso-propoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-propoxy-4- [N-methyl- (4-iso-propoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-iso-propoxy-4- [N-methyl- (4-iso-propoxyphenyl) amino] -5 -(Trifluoromethyl) pyrimidine, 2-n-butoxy-4- [N-methyl- (4-iso-propoxyphenyl) amino] -5- ( Trifluoromethyl) pyrimidine, 2-iso-butoxy-4- [N-methyl- (4-iso-propoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-sec-butoxy-4- [N- Methyl- (4-iso-propoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-tert-butoxy-4- [N-methyl- (4-iso-propoxyphenyl) amino] -5- (tri Fluoromethyl) pyrimidine, 2-n-pentoxy-4- [N-methyl- (4-iso-propoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-cyclo-pentoxy-4- [N-methyl -(4-Iso-propoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-hexylo Ci-4- [N-methyl- (4-iso-propoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-cyclo-hexyloxy-4- [N-methyl- (4-iso-propoxyphenyl) ) Amino] -5- (trifluoromethyl) pyrimidine and the like.
本発明の一般式(1)で表わされる2−アルコキシ−5−(トリフルオロメチル)ピリミジン誘導体でR1がn−ブトキシ基である化合物としては、具体的には例えば、2−メトキシ−4−[N−メチル−(2−n−ブトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−エトキシ−4−[N−メチル−(2−n−ブトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−プロポキシ−4−[N−メチル−(2−n−ブトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−プロポキシ−4−[N−メチル−(2−n−ブトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−iso−プロポキシ−4−[N−メチル−(2−n−ブトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ブトキシ−4−[N−メチル−(2−n−ブトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−iso−ブトキシ−4−[N−メチル−(2−n−ブトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−sec−ブトキシ−4−[N−メチル−(2−n−ブトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−tert−ブトキシ−4−[N−メチル−(2−n−ブトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ペントキシ−4−[N−メチル−(2−n−ブトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−cyclo−ペントキシ−4−[N−メチル−(2−n−ブトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ヘキシルオキシ−4−[N−メチル−(2−n−ブトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−cyclo−ヘキシルオキシ−4−[N−メチル−(2−n−ブトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−メトキシ−4−[N−メチル−(3−n−ブトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−エトキシ−4−[N−メチル−(3−n−ブトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−プロポキシ−4−[N−メチル−(3−n−ブトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−プロポキシ−4−[N−メチル−(3−n−ブトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−iso−プロポキシ−4−[N−メチル−(3−n−ブトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ブトキシ−4−[N−メチル−(3−n−ブトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−iso−ブトキシ−4−[N−メチル−(3−n−ブトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−sec−ブトキシ−4−[N−メチル−(3−n−ブトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−tert−ブトキシ−4−[N−メチル−(3−n−ブトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ペントキシ−4−[N−メチル−(3−n−ブトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−cyclo−ペントキシ−4−[N−メチル−(3−n−ブトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ヘキシルオキシ−4−[N−メチル−(3−n−ブトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−cyclo−ヘキシルオキシ−4−[N−メチル−(3−n−ブトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−メトキシ−4−[N−メチル−(4−n−ブトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−エトキシ−4−[N−メチル−(4−n−ブトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−プロポキシ−4−[N−メチル−(4−n−ブトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−プロポキシ−4−[N−メチル−(4−n−ブトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−iso−プロポキシ−4−[N−メチル−(4−n−ブトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ブトキシ−4−[N−メチル−(4−n−ブトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−iso−ブトキシ−4−[N−メチル−(4−n−ブトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−sec−ブトキシ−4−[N−メチル−(4−n−ブトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−tert−ブトキシ−4−[N−メチル−(4−n−ブトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ペントキシ−4−[N−メチル−(4−n−ブトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−cyclo−ペントキシ−4−[N−メチル−(4−n−ブトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ヘキシルオキシ−4−[N−メチル−(4−n−ブトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−cyclo−ヘキシルオキシ−4−[N−メチル−(4−n−ブトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン等が挙げられる。 Specific examples of the 2-alkoxy-5- (trifluoromethyl) pyrimidine derivative represented by the general formula (1) of the present invention in which R 1 is an n-butoxy group include 2-methoxy-4- [N-methyl- (2-n-butoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-ethoxy-4- [N-methyl- (2-n-butoxyphenyl) amino] -5- ( Trifluoromethyl) pyrimidine, 2-n-propoxy-4- [N-methyl- (2-n-butoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-propoxy-4- [N- Methyl- (2-n-butoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-iso-propoxy-4- [N-methyl- (2-n-butoxyphenyl) Mino] -5- (trifluoromethyl) pyrimidine, 2-n-butoxy-4- [N-methyl- (2-n-butoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-iso-butoxy -4- [N-methyl- (2-n-butoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-sec-butoxy-4- [N-methyl- (2-n-butoxyphenyl) amino ] -5- (trifluoromethyl) pyrimidine, 2-tert-butoxy-4- [N-methyl- (2-n-butoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-pentoxy- 4- [N-methyl- (2-n-butoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-cyclo-pentoxy-4- [N-methyl -(2-n-Butoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-hexyloxy-4- [N-methyl- (2-n-butoxyphenyl) amino] -5- (tri Fluoromethyl) pyrimidine, 2-cyclo-hexyloxy-4- [N-methyl- (2-n-butoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-methoxy-4- [N-methyl- (3-n-Butoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-ethoxy-4- [N-methyl- (3-n-butoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine 2-n-propoxy-4- [N-methyl- (3-n-butoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-propo Ci-4- [N-methyl- (3-n-butoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-iso-propoxy-4- [N-methyl- (3-n-butoxyphenyl) Amino] -5- (trifluoromethyl) pyrimidine, 2-n-butoxy-4- [N-methyl- (3-n-butoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-iso-butoxy -4- [N-methyl- (3-n-butoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-sec-butoxy-4- [N-methyl- (3-n-butoxyphenyl) amino ] -5- (trifluoromethyl) pyrimidine, 2-tert-butoxy-4- [N-methyl- (3-n-butoxyphenyl) amino] -5- (trifluoromethyl) Pyrimidine, 2-n-pentoxy-4- [N-methyl- (3-n-butoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-cyclo-pentoxy-4- [N-methyl- (3 -N-butoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-hexyloxy-4- [N-methyl- (3-n-butoxyphenyl) amino] -5- (trifluoromethyl) Pyrimidine, 2-cyclo-hexyloxy-4- [N-methyl- (3-n-butoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-methoxy-4- [N-methyl- (4- n-butoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-ethoxy-4- [N-methyl- (4-n-butoxyphenyl) amino ] -5- (trifluoromethyl) pyrimidine, 2-n-propoxy-4- [N-methyl- (4-n-butoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-propoxy- 4- [N-methyl- (4-n-butoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-iso-propoxy-4- [N-methyl- (4-n-butoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-butoxy-4- [N-methyl- (4-n-butoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-iso-butoxy-4 -[N-methyl- (4-n-butoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-sec-butoxy-4- [N-methyl- (4-n- Toxiphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-tert-butoxy-4- [N-methyl- (4-n-butoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2- n-pentoxy-4- [N-methyl- (4-n-butoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-cyclo-pentoxy-4- [N-methyl- (4-n-butoxy) Phenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-hexyloxy-4- [N-methyl- (4-n-butoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2- cyclo-hexyloxy-4- [N-methyl- (4-n-butoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine and the like It is below.
本発明の一般式(1)で表わされる2−アルコキシ−5−(トリフルオロメチル)ピリミジン誘導体でR1がiso−ブトキシ基である化合物としては、具体的には例えば、2−メトキシ−4−[N−メチル−(2−iso−ブトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−エトキシ−4−[N−メチル−(2−iso−ブトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−プロポキシ−4−[N−メチル−(2−iso−ブトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−プロポキシ−4−[N−メチル−(2−iso−ブトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−iso−プロポキシ−4−[N−メチル−(2−iso−ブトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ブトキシ−4−[N−メチル−(2−iso−ブトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−iso−ブトキシ−4−[N−メチル−(2−iso−ブトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−sec−ブトキシ−4−[N−メチル−(2−iso−ブトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−tert−ブトキシ−4−[N−メチル−(2−iso−ブトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ペントキシ−4−[N−メチル−(2−iso−ブトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−cyclo−ペントキシ−4−[N−メチル−(2−iso−ブトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ヘキシルオキシ−4−[N−メチル−(2−iso−ブトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−cyclo−ヘキシルオキシ−4−[N−メチル−(2−iso−ブトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−メトキシ−4−[N−メチル−(3−iso−ブトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−エトキシ−4−[N−メチル−(3−iso−ブトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−プロポキシ−4−[N−メチル−(3−iso−ブトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−プロポキシ−4−[N−メチル−(3−iso−ブトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−iso−プロポキシ−4−[N−メチル−(3−iso−ブトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ブトキシ−4−[N−メチル−(3−iso−ブトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−iso−ブトキシ−4−[N−メチル−(3−iso−ブトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−sec−ブトキシ−4−[N−メチル−(3−iso−ブトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−tert−ブトキシ−4−[N−メチル−(3−iso−ブトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ペントキシ−4−[N−メチル−(3−iso−ブトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−cyclo−ペントキシ−4−[N−メチル−(3−iso−ブトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ヘキシルオキシ−4−[N−メチル−(3−iso−ブトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−cyclo−ヘキシルオキシ−4−[N−メチル−(3−iso−ブトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−メトキシ−4−[N−メチル−(4−iso−ブトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−エトキシ−4−[N−メチル−(4−iso−ブトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−プロポキシ−4−[N−メチル−(4−iso−ブトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−プロポキシ−4−[N−メチル−(4−iso−ブトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−iso−プロポキシ−4−[N−メチル−(4−iso−ブトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ブトキシ−4−[N−メチル−(4−iso−ブトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−iso−ブトキシ−4−[N−メチル−(4−iso−ブトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−sec−ブトキシ−4−[N−メチル−(4−iso−ブトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−tert−ブトキシ−4−[N−メチル−(4−iso−ブトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ペントキシ−4−[N−メチル−(4−iso−ブトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−cyclo−ペントキシ−4−[N−メチル−(4−iso−ブトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ヘキシルオキシ−4−[N−メチル−(4−iso−ブトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−cyclo−ヘキシルオキシ−4−[N−メチル−(4−iso−ブトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン等が挙げられる。 Specific examples of the 2-alkoxy-5- (trifluoromethyl) pyrimidine derivative represented by the general formula (1) of the present invention in which R 1 is an iso-butoxy group include 2-methoxy-4- [N-methyl- (2-iso-butoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-ethoxy-4- [N-methyl- (2-iso-butoxyphenyl) amino] -5- ( Trifluoromethyl) pyrimidine, 2-n-propoxy-4- [N-methyl- (2-iso-butoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-propoxy-4- [N- Methyl- (2-iso-butoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-iso-propoxy-4- [N-methyl- (2-i o-butoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-butoxy-4- [N-methyl- (2-iso-butoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-iso-butoxy-4- [N-methyl- (2-iso-butoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-sec-butoxy-4- [N-methyl- (2-iso -Butoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-tert-butoxy-4- [N-methyl- (2-iso-butoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2 -N-pentoxy-4- [N-methyl- (2-iso-butoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-cyclo-pentoxy-4- [N-methyl- (2-iso-butoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-hexyloxy-4- [N-methyl- (2- iso-butoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-cyclo-hexyloxy-4- [N-methyl- (2-iso-butoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine 2-methoxy-4- [N-methyl- (3-iso-butoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-ethoxy-4- [N-methyl- (3-iso-butoxyphenyl) ) Amino] -5- (trifluoromethyl) pyrimidine, 2-n-propoxy-4- [N-methyl- (3-iso-butoxyphe) L) amino] -5- (trifluoromethyl) pyrimidine, 2-n-propoxy-4- [N-methyl- (3-iso-butoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-iso -Propoxy-4- [N-methyl- (3-iso-butoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-butoxy-4- [N-methyl- (3-iso-butoxyphenyl) ) Amino] -5- (trifluoromethyl) pyrimidine, 2-iso-butoxy-4- [N-methyl- (3-iso-butoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-sec- Butoxy-4- [N-methyl- (3-iso-butoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-tert-butyl Xyl-4- [N-methyl- (3-iso-butoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-pentoxy-4- [N-methyl- (3-iso-butoxyphenyl) Amino] -5- (trifluoromethyl) pyrimidine, 2-cyclo-pentoxy-4- [N-methyl- (3-iso-butoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-hexyl Oxy-4- [N-methyl- (3-iso-butoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-cyclo-hexyloxy-4- [N-methyl- (3-iso-butoxyphenyl) Amino] -5- (trifluoromethyl) pyrimidine, 2-methoxy-4- [N-methyl- (4-iso-butoxyphenyl) a Mino] -5- (trifluoromethyl) pyrimidine, 2-ethoxy-4- [N-methyl- (4-iso-butoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-propoxy-4 -[N-methyl- (4-iso-butoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-propoxy-4- [N-methyl- (4-iso-butoxyphenyl) amino]- 5- (trifluoromethyl) pyrimidine, 2-iso-propoxy-4- [N-methyl- (4-iso-butoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-butoxy-4- [N-methyl- (4-iso-butoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-iso-butoxy-4- [N-me Ru- (4-iso-butoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-sec-butoxy-4- [N-methyl- (4-iso-butoxyphenyl) amino] -5- (tri Fluoromethyl) pyrimidine, 2-tert-butoxy-4- [N-methyl- (4-iso-butoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-pentoxy-4- [N-methyl -(4-Iso-butoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-cyclo-pentoxy-4- [N-methyl- (4-iso-butoxyphenyl) amino] -5- (trifluoro Methyl) pyrimidine, 2-n-hexyloxy-4- [N-methyl- (4-iso-butoxyphenyl) amino] -5- (tri Ruoromechiru) pyrimidine, 2-cyclo- hexyloxy-4-[N-methyl - (4-an iso-butoxyphenyl) amino] -5- (trifluoromethyl) include pyrimidine and the like.
本発明の一般式(1)で表わされる2−アルコキシ−5−(トリフルオロメチル)ピリミジン誘導体でR1がsec−ブトキシ基である化合物としては、具体的には例えば、2−メトキシ−4−[N−メチル−(2−sec−ブトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−エトキシ−4−[N−メチル−(2−sec−ブトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−プロポキシ−4−[N−メチル−(2−sec−ブトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−プロポキシ−4−[N−メチル−(2−sec−ブトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−iso−プロポキシ−4−[N−メチル−(2−sec−ブトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ブトキシ−4−[N−メチル−(2−sec−ブトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−iso−ブトキシ−4−[N−メチル−(2−sec−ブトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−sec−ブトキシ−4−[N−メチル−(2−sec−ブトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−tert−ブトキシ−4−[N−メチル−(2−sec−ブトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ペントキシ−4−[N−メチル−(2−sec−ブトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−cyclo−ペントキシ−4−[N−メチル−(2−sec−ブトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ヘキシルオキシ−4−[N−メチル−(2−sec−ブトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−cyclo−ヘキシルオキシ−4−[N−メチル−(2−sec−ブトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−メトキシ−4−[N−メチル−(3−sec−ブトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−エトキシ−4−[N−メチル−(3−sec−ブトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−プロポキシ−4−[N−メチル−(3−sec−ブトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−プロポキシ−4−[N−メチル−(3−sec−ブトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−iso−プロポキシ−4−[N−メチル−(3−sec−ブトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ブトキシ−4−[N−メチル−(3−sec−ブトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−iso−ブトキシ−4−[N−メチル−(3−sec−ブトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−sec−ブトキシ−4−[N−メチル−(3−sec−ブトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−tert−ブトキシ−4−[N−メチル−(3−sec−ブトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ペントキシ−4−[N−メチル−(3−sec−ブトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−cyclo−ペントキシ−4−[N−メチル−(3−sec−ブトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ヘキシルオキシ−4−[N−メチル−(3−sec−ブトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−cyclo−ヘキシルオキシ−4−[N−メチル−(3−sec−ブトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−メトキシ−4−[N−メチル−(4−sec−ブトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−エトキシ−4−[N−メチル−(4−sec−ブトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−プロポキシ−4−[N−メチル−(4−sec−ブトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−プロポキシ−4−[N−メチル−(4−sec−ブトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−iso−プロポキシ−4−[N−メチル−(4−sec−ブトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ブトキシ−4−[N−メチル−(4−sec−ブトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−iso−ブトキシ−4−[N−メチル−(4−sec−ブトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−sec−ブトキシ−4−[N−メチル−(4−sec−ブトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−tert−ブトキシ−4−[N−メチル−(4−sec−ブトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ペントキシ−4−[N−メチル−(4−sec−ブトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−cyclo−ペントキシ−4−[N−メチル−(4−sec−ブトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ヘキシルオキシ−4−[N−メチル−(4−sec−ブトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−cyclo−ヘキシルオキシ−4−[N−メチル−(4−sec−ブトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン等が挙げられる。 Specific examples of the 2-alkoxy-5- (trifluoromethyl) pyrimidine derivative represented by the general formula (1) of the present invention in which R 1 is a sec-butoxy group include 2-methoxy-4- [N-methyl- (2-sec-butoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-ethoxy-4- [N-methyl- (2-sec-butoxyphenyl) amino] -5- ( Trifluoromethyl) pyrimidine, 2-n-propoxy-4- [N-methyl- (2-sec-butoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-propoxy-4- [N- Methyl- (2-sec-butoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-iso-propoxy-4- [N-methyl- (2-s c-butoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-butoxy-4- [N-methyl- (2-sec-butoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-iso-butoxy-4- [N-methyl- (2-sec-butoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-sec-butoxy-4- [N-methyl- (2-sec -Butoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-tert-butoxy-4- [N-methyl- (2-sec-butoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2 -N-pentoxy-4- [N-methyl- (2-sec-butoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-cyclo-pentoxy-4- [N-methyl- (2-sec-butoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-hexyloxy-4- [N-methyl- (2- sec-butoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-cyclo-hexyloxy-4- [N-methyl- (2-sec-butoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine 2-methoxy-4- [N-methyl- (3-sec-butoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-ethoxy-4- [N-methyl- (3-sec-butoxyphenyl) ) Amino] -5- (trifluoromethyl) pyrimidine, 2-n-propoxy-4- [N-methyl- (3-sec-butoxyphe) L) amino] -5- (trifluoromethyl) pyrimidine, 2-n-propoxy-4- [N-methyl- (3-sec-butoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-iso -Propoxy-4- [N-methyl- (3-sec-butoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-butoxy-4- [N-methyl- (3-sec-butoxyphenyl) ) Amino] -5- (trifluoromethyl) pyrimidine, 2-iso-butoxy-4- [N-methyl- (3-sec-butoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-sec- Butoxy-4- [N-methyl- (3-sec-butoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-tert-butyl Xyl-4- [N-methyl- (3-sec-butoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-pentoxy-4- [N-methyl- (3-sec-butoxyphenyl) Amino] -5- (trifluoromethyl) pyrimidine, 2-cyclo-pentoxy-4- [N-methyl- (3-sec-butoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-hexyl Oxy-4- [N-methyl- (3-sec-butoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-cyclo-hexyloxy-4- [N-methyl- (3-sec-butoxyphenyl) Amino] -5- (trifluoromethyl) pyrimidine, 2-methoxy-4- [N-methyl- (4-sec-butoxyphenyl) a Mino] -5- (trifluoromethyl) pyrimidine, 2-ethoxy-4- [N-methyl- (4-sec-butoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-propoxy-4 -[N-methyl- (4-sec-butoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-propoxy-4- [N-methyl- (4-sec-butoxyphenyl) amino]- 5- (trifluoromethyl) pyrimidine, 2-iso-propoxy-4- [N-methyl- (4-sec-butoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-butoxy-4- [N-methyl- (4-sec-butoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-iso-butoxy-4- [N-me Ru- (4-sec-butoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-sec-butoxy-4- [N-methyl- (4-sec-butoxyphenyl) amino] -5- (tri Fluoromethyl) pyrimidine, 2-tert-butoxy-4- [N-methyl- (4-sec-butoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-pentoxy-4- [N-methyl -(4-sec-butoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-cyclo-pentoxy-4- [N-methyl- (4-sec-butoxyphenyl) amino] -5- (trifluoro Methyl) pyrimidine, 2-n-hexyloxy-4- [N-methyl- (4-sec-butoxyphenyl) amino] -5- (tri Ruoromechiru) pyrimidine, 2-cyclo- hexyloxy-4-[N-methyl - (4-sec-butoxyphenyl) amino] -5- (trifluoromethyl) include pyrimidine and the like.
本発明の一般式(1)で表わされる2−アルコキシ−5−(トリフルオロメチル)ピリミジン誘導体でR1がtert−ブトキシ基である化合物としては、具体的には例えば、2−メトキシ−4−[N−メチル−(2−tert−ブトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−エトキシ−4−[N−メチル−(2−tert−ブトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−プロポキシ−4−[N−メチル−(2−tert−ブトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−プロポキシ−4−[N−メチル−(2−tert−ブトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−iso−プロポキシ−4−[N−メチル−(2−tert−ブトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ブトキシ−4−[N−メチル−(2−tert−ブトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−iso−ブトキシ−4−[N−メチル−(2−tert−ブトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−sec−ブトキシ−4−[N−メチル−(2−tert−ブトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−tert−ブトキシ−4−[N−メチル−(2−tert−ブトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ペントキシ−4−[N−メチル−(2−tert−ブトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−cyclo−ペントキシ−4−[N−メチル−(2−tert−ブトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ヘキシルオキシ−4−[N−メチル−(2−tert−ブトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−cyclo−ヘキシルオキシ−4−[N−メチル−(2−tert−ブトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−メトキシ−4−[N−メチル−(3−tert−ブトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−エトキシ−4−[N−メチル−(3−tert−ブトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−プロポキシ−4−[N−メチル−(3−tert−ブトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−プロポキシ−4−[N−メチル−(3−tert−ブトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−iso−プロポキシ−4−[N−メチル−(3−tert−ブトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ブトキシ−4−[N−メチル−(3−tert−ブトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−iso−ブトキシ−4−[N−メチル−(3−tert−ブトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−sec−ブトキシ−4−[N−メチル−(3−tert−ブトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−tert−ブトキシ−4−[N−メチル−(3−tert−ブトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ペントキシ−4−[N−メチル−(3−tert−ブトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−cyclo−ペントキシ−4−[N−メチル−(3−tert−ブトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ヘキシルオキシ−4−[N−メチル−(3−tert−ブトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−cyclo−ヘキシルオキシ−4−[N−メチル−(3−tert−ブトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−メトキシ−4−[N−メチル−(4−tert−ブトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−エトキシ−4−[N−メチル−(4−tert−ブトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−プロポキシ−4−[N−メチル−(4−tert−ブトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−プロポキシ−4−[N−メチル−(4−tert−ブトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−iso−プロポキシ−4−[N−メチル−(4−tert−ブトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ブトキシ−4−[N−メチル−(4−tert−ブトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−iso−ブトキシ−4−[N−メチル−(4−tert−ブトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−sec−ブトキシ−4−[N−メチル−(4−tert−ブトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−tert−ブトキシ−4−[N−メチル−(4−tert−ブトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ペントキシ−4−[N−メチル−(4−tert−ブトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−cyclo−ペントキシ−4−[N−メチル−(4−tert−ブトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ヘキシルオキシ−4−[N−メチル−(4−tert−ブトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−cyclo−ヘキシルオキシ−4−[N−メチル−(4−tert−ブトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン等が挙げられる。 Specific examples of the 2-alkoxy-5- (trifluoromethyl) pyrimidine derivative represented by the general formula (1) of the present invention in which R 1 is a tert-butoxy group include 2-methoxy-4- [N-methyl- (2-tert-butoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-ethoxy-4- [N-methyl- (2-tert-butoxyphenyl) amino] -5- ( Trifluoromethyl) pyrimidine, 2-n-propoxy-4- [N-methyl- (2-tert-butoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-propoxy-4- [N- Methyl- (2-tert-butoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-iso-propoxy-4- [N-methyl (2-tert-Butoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-butoxy-4- [N-methyl- (2-tert-butoxyphenyl) amino] -5- (trifluoromethyl ) Pyrimidine, 2-iso-butoxy-4- [N-methyl- (2-tert-butoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-sec-butoxy-4- [N-methyl- ( 2-tert-butoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-tert-butoxy-4- [N-methyl- (2-tert-butoxyphenyl) amino] -5- (trifluoromethyl) Pyrimidine, 2-n-pentoxy-4- [N-methyl- (2-tert-butoxyphenyl) amino] -5- (trifluoro (Romethyl) pyrimidine, 2-cyclo-pentoxy-4- [N-methyl- (2-tert-butoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-hexyloxy-4- [N-methyl -(2-tert-Butoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-cyclo-hexyloxy-4- [N-methyl- (2-tert-butoxyphenyl) amino] -5- (tri Fluoromethyl) pyrimidine, 2-methoxy-4- [N-methyl- (3-tert-butoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-ethoxy-4- [N-methyl- (3- tert-butoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-propoxy-4- [N-me Ru- (3-tert-butoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-propoxy-4- [N-methyl- (3-tert-butoxyphenyl) amino] -5- (tri Fluoromethyl) pyrimidine, 2-iso-propoxy-4- [N-methyl- (3-tert-butoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-butoxy-4- [N-methyl -(3-tert-butoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-iso-butoxy-4- [N-methyl- (3-tert-butoxyphenyl) amino] -5- (trifluoro Methyl) pyrimidine, 2-sec-butoxy-4- [N-methyl- (3-tert-butoxyphenyl) amino] -5- (tri Fluoromethyl) pyrimidine, 2-tert-butoxy-4- [N-methyl- (3-tert-butoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-pentoxy-4- [N-methyl- (3-tert-Butoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-cyclo-pentoxy-4- [N-methyl- (3-tert-butoxyphenyl) amino] -5- (trifluoromethyl) ) Pyrimidine, 2-n-hexyloxy-4- [N-methyl- (3-tert-butoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-cyclo-hexyloxy-4- [N-methyl -(3-tert-butoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-methoxy -4- [N-methyl- (4-tert-butoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-ethoxy-4- [N-methyl- (4-tert-butoxyphenyl) amino]- 5- (trifluoromethyl) pyrimidine, 2-n-propoxy-4- [N-methyl- (4-tert-butoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-propoxy-4- [N-methyl- (4-tert-butoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-iso-propoxy-4- [N-methyl- (4-tert-butoxyphenyl) amino] -5 -(Trifluoromethyl) pyrimidine, 2-n-butoxy-4- [N-methyl- (4-tert-butoxyphenyl) amino] -5- ( Trifluoromethyl) pyrimidine, 2-iso-butoxy-4- [N-methyl- (4-tert-butoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-sec-butoxy-4- [N- Methyl- (4-tert-butoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-tert-butoxy-4- [N-methyl- (4-tert-butoxyphenyl) amino] -5- (tri Fluoromethyl) pyrimidine, 2-n-pentoxy-4- [N-methyl- (4-tert-butoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-cyclo-pentoxy-4- [N-methyl -(4-tert-butoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-hexylo Ci-4- [N-methyl- (4-tert-butoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-cyclo-hexyloxy-4- [N-methyl- (4-tert-butoxyphenyl) ) Amino] -5- (trifluoromethyl) pyrimidine and the like.
本発明の一般式(1)で表わされる2−アルコキシ−5−(トリフルオロメチル)ピリミジン誘導体でR1がn−ペントキシ基である化合物としては、具体的には例えば、2−メトキシ−4−[N−メチル−(2−n−ペントキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−エトキシ−4−[N−メチル−(2−n−ペントキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−プロポキシ−4−[N−メチル−(2−n−ペントキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−プロポキシ−4−[N−メチル−(2−n−ペントキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−iso−プロポキシ−4−[N−メチル−(2−n−ペントキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ブトキシ−4−[N−メチル−(2−n−ペントキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−iso−ブトキシ−4−[N−メチル−(2−n−ペントキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−sec−ブトキシ−4−[N−メチル−(2−n−ペントキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−tert−ブトキシ−4−[N−メチル−(2−n−ペントキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ペントキシ−4−[N−メチル−(2−n−ペントキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−cyclo−ペントキシ−4−[N−メチル−(2−n−ペントキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ヘキシルオキシ−4−[N−メチル−(2−n−ペントキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−cyclo−ヘキシルオキシ−4−[N−メチル−(2−n−ペントキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−メトキシ−4−[N−メチル−(3−n−ペントキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−エトキシ−4−[N−メチル−(3−n−ペントキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−プロポキシ−4−[N−メチル−(3−n−ペントキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−プロポキシ−4−[N−メチル−(3−n−ペントキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−iso−プロポキシ−4−[N−メチル−(3−n−ペントキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ブトキシ−4−[N−メチル−(3−n−ペントキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−iso−ブトキシ−4−[N−メチル−(3−n−ペントキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−sec−ブトキシ−4−[N−メチル−(3−n−ペントキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−tert−ブトキシ−4−[N−メチル−(3−n−ペントキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ペントキシ−4−[N−メチル−(3−n−ペントキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−cyclo−ペントキシ−4−[N−メチル−(3−n−ペントキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ヘキシルオキシ−4−[N−メチル−(3−n−ペントキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−cyclo−ヘキシルオキシ−4−[N−メチル−(3−n−ペントキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−メトキシ−4−[N−メチル−(4−n−ペントキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−エトキシ−4−[N−メチル−(4−n−ペントキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−プロポキシ−4−[N−メチル−(4−n−ペントキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−プロポキシ−4−[N−メチル−(4−n−ペントキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−iso−プロポキシ−4−[N−メチル−(4−n−ペントキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ブトキシ−4−[N−メチル−(4−n−ペントキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−iso−ブトキシ−4−[N−メチル−(4−n−ペントキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−sec−ブトキシ−4−[N−メチル−(4−n−ペントキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−tert−ブトキシ−4−[N−メチル−(4−n−ペントキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ペントキシ−4−[N−メチル−(4−n−ペントキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−cyclo−ペントキシ−4−[N−メチル−(4−n−ペントキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ヘキシルオキシ−4−[N−メチル−(4−n−ペントキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−cyclo−ヘキシルオキシ−4−[N−メチル−(4−n−ペントキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン等が挙げられる。 Specific examples of the 2-alkoxy-5- (trifluoromethyl) pyrimidine derivative represented by the general formula (1) of the present invention in which R 1 is an n-pentoxy group include 2-methoxy-4- [N-methyl- (2-n-pentoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-ethoxy-4- [N-methyl- (2-n-pentoxyphenyl) amino] -5 -(Trifluoromethyl) pyrimidine, 2-n-propoxy-4- [N-methyl- (2-n-pentoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-propoxy-4- [N-methyl- (2-n-pentoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-iso-propoxy-4- [N-methyl- (2-n-pentoxy) Phenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-butoxy-4- [N-methyl- (2-n-pentoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2- iso-butoxy-4- [N-methyl- (2-n-pentoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-sec-butoxy-4- [N-methyl- (2-n- Pentoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-tert-butoxy-4- [N-methyl- (2-n-pentoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-pentoxy-4- [N-methyl- (2-n-pentoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-cyclo-pent Xyl-4- [N-methyl- (2-n-pentoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-hexyloxy-4- [N-methyl- (2-n-pen) Toxiphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-cyclo-hexyloxy-4- [N-methyl- (2-n-pentoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-methoxy-4- [N-methyl- (3-n-pentoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-ethoxy-4- [N-methyl- (3-n-pentoxy) Phenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-propoxy-4- [N-methyl- (3-n-pentoxyphenyl) amino] -5- (trifluoro Til) pyrimidine, 2-n-propoxy-4- [N-methyl- (3-n-pentoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-iso-propoxy-4- [N-methyl -(3-n-pentoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-butoxy-4- [N-methyl- (3-n-pentoxyphenyl) amino] -5- ( Trifluoromethyl) pyrimidine, 2-iso-butoxy-4- [N-methyl- (3-n-pentoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-sec-butoxy-4- [N -Methyl- (3-n-pentoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-tert-butoxy-4- [N-methyl- (3-n-pentoxy) Phenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-pentoxy-4- [N-methyl- (3-n-pentoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2- cyclo-pentoxy-4- [N-methyl- (3-n-pentoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-hexyloxy-4- [N-methyl- (3-n -Pentoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-cyclo-hexyloxy-4- [N-methyl- (3-n-pentoxyphenyl) amino] -5- (trifluoromethyl) Pyrimidine, 2-methoxy-4- [N-methyl- (4-n-pentoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-ethoxy Ci-4- [N-methyl- (4-n-pentoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-propoxy-4- [N-methyl- (4-n-pentoxy) Phenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-propoxy-4- [N-methyl- (4-n-pentoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2- iso-propoxy-4- [N-methyl- (4-n-pentoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-butoxy-4- [N-methyl- (4-n- Pentoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-iso-butoxy-4- [N-methyl- (4-n-pentoxyphenyl) amino] -5- (trifluorome ) Pyrimidine, 2-sec-butoxy-4- [N-methyl- (4-n-pentoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-tert-butoxy-4- [N-methyl] -(4-n-pentoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-pentoxy-4- [N-methyl- (4-n-pentoxyphenyl) amino] -5- ( Trifluoromethyl) pyrimidine, 2-cyclo-pentoxy-4- [N-methyl- (4-n-pentoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-hexyloxy-4- [ N-methyl- (4-n-pentoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-cyclo-hexyloxy-4- [N-methyl- 4-n-pentoxy phenyl) amino] -5- (trifluoromethyl) pyrimidine, and the like.
本発明の一般式(1)で表わされる2−アルコキシ−5−(トリフルオロメチル)ピリミジン誘導体でR1がcyclo−ペントキシ基である化合物としては、具体的には例えば、2−メトキシ−4−[N−メチル−(2−cyclo−ペントキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−エトキシ−4−[N−メチル−(2−cyclo−ペントキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−プロポキシ−4−[N−メチル−(2−cyclo−ペントキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−プロポキシ−4−[N−メチル−(2−cyclo−ペントキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−iso−プロポキシ−4−[N−メチル−(2−cyclo−ペントキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ブトキシ−4−[N−メチル−(2−cyclo−ペントキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−iso−ブトキシ−4−[N−メチル−(2−cyclo−ペントキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−sec−ブトキシ−4−[N−メチル−(2−cyclo−ペントキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−tert−ブトキシ−4−[N−メチル−(2−cyclo−ペントキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ペントキシ−4−[N−メチル−(2−cyclo−ペントキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−cyclo−ペントキシ−4−[N−メチル−(2−cyclo−ペントキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ヘキシルオキシ−4−[N−メチル−(2−cyclo−ペントキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−cyclo−ヘキシルオキシ−4−[N−メチル−(2−cyclo−ペントキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−メトキシ−4−[N−メチル−(3−cyclo−ペントキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−エトキシ−4−[N−メチル−(3−cyclo−ペントキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−プロポキシ−4−[N−メチル−(3−cyclo−ペントキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−プロポキシ−4−[N−メチル−(3−cyclo−ペントキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−iso−プロポキシ−4−[N−メチル−(3−cyclo−ペントキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ブトキシ−4−[N−メチル−(3−cyclo−ペントキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−iso−ブトキシ−4−[N−メチル−(3−cyclo−ペントキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−sec−ブトキシ−4−[N−メチル−(3−cyclo−ペントキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−tert−ブトキシ−4−[N−メチル−(3−cyclo−ペントキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ペントキシ−4−[N−メチル−(3−cyclo−ペントキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−cyclo−ペントキシ−4−[N−メチル−(3−cyclo−ペントキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ヘキシルオキシ−4−[N−メチル−(3−cyclo−ペントキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−cyclo−ヘキシルオキシ−4−[N−メチル−(3−cyclo−ペントキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−メトキシ−4−[N−メチル−(4−cyclo−ペントキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−エトキシ−4−[N−メチル−(4−cyclo−ペントキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−プロポキシ−4−[N−メチル−(4−cyclo−ペントキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−プロポキシ−4−[N−メチル−(4−cyclo−ペントキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−iso−プロポキシ−4−[N−メチル−(4−cyclo−ペントキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ブトキシ−4−[N−メチル−(4−cyclo−ペントキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−iso−ブトキシ−4−[N−メチル−(4−cyclo−ペントキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−sec−ブトキシ−4−[N−メチル−(4−cyclo−ペントキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−tert−ブトキシ−4−[N−メチル−(4−cyclo−ペントキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ペントキシ−4−[N−メチル−(4−cyclo−ペントキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−cyclo−ペントキシ−4−[N−メチル−(4−cyclo−ペントキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ヘキシルオキシ−4−[N−メチル−(4−cyclo−ペントキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−cyclo−ヘキシルオキシ−4−[N−メチル−(4−cyclo−ペントキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン等が挙げられる。 Specific examples of the 2-alkoxy-5- (trifluoromethyl) pyrimidine derivative represented by the general formula (1) of the present invention in which R 1 is a cyclo-pentoxy group include 2-methoxy-4- [N-methyl- (2-cyclo-pentoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-ethoxy-4- [N-methyl- (2-cyclo-pentoxyphenyl) amino] -5 -(Trifluoromethyl) pyrimidine, 2-n-propoxy-4- [N-methyl- (2-cyclo-pentoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-propoxy-4- [N-methyl- (2-cyclo-pentoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-iso-propoxy -4- [N-methyl- (2-cyclo-pentoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-butoxy-4- [N-methyl- (2-cyclo-pentoxyphenyl) ) Amino] -5- (trifluoromethyl) pyrimidine, 2-iso-butoxy-4- [N-methyl- (2-cyclo-pentoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-sec -Butoxy-4- [N-methyl- (2-cyclo-pentoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-tert-butoxy-4- [N-methyl- (2-cyclo-pen) Toxiphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-pentoxy-4- [N-methyl- (2-cyclo-pe) Toxoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-cyclo-pentoxy-4- [N-methyl- (2-cyclo-pentoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-hexyloxy-4- [N-methyl- (2-cyclo-pentoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-cyclo-hexyloxy-4- [N-methyl- ( 2-cyclo-pentoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-methoxy-4- [N-methyl- (3-cyclo-pentoxyphenyl) amino] -5- (trifluoromethyl) Pyrimidine, 2-ethoxy-4- [N-methyl- (3-cyclo-pentoxyphenyl) amino] -5- ( Rifluoromethyl) pyrimidine, 2-n-propoxy-4- [N-methyl- (3-cyclo-pentoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-propoxy-4- [N -Methyl- (3-cyclo-pentoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-iso-propoxy-4- [N-methyl- (3-cyclo-pentoxyphenyl) amino] -5 -(Trifluoromethyl) pyrimidine, 2-n-butoxy-4- [N-methyl- (3-cyclo-pentoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-iso-butoxy-4- [N-methyl- (3-cyclo-pentoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-sec Butoxy-4- [N-methyl- (3-cyclo-pentoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-tert-butoxy-4- [N-methyl- (3-cyclo-pentoxy) Phenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-pentoxy-4- [N-methyl- (3-cyclo-pentoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2- cyclo-pentoxy-4- [N-methyl- (3-cyclo-pentoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-hexyloxy-4- [N-methyl- (3-cyclo) -Pentoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-cyclo-hexyloxy-4- [N -Methyl- (3-cyclo-pentoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-methoxy-4- [N-methyl- (4-cyclo-pentoxyphenyl) amino] -5- ( Trifluoromethyl) pyrimidine, 2-ethoxy-4- [N-methyl- (4-cyclo-pentoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-propoxy-4- [N-methyl -(4-cyclo-pentoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-propoxy-4- [N-methyl- (4-cyclo-pentoxyphenyl) amino] -5- ( Trifluoromethyl) pyrimidine, 2-iso-propoxy-4- [N-methyl- (4-cyclo-pentoxyphenyl) amino -5- (trifluoromethyl) pyrimidine, 2-n-butoxy-4- [N-methyl- (4-cyclo-pentoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-iso-butoxy- 4- [N-methyl- (4-cyclo-pentoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-sec-butoxy-4- [N-methyl- (4-cyclo-pentoxyphenyl) Amino] -5- (trifluoromethyl) pyrimidine, 2-tert-butoxy-4- [N-methyl- (4-cyclo-pentoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n- Pentoxy-4- [N-methyl- (4-cyclo-pentoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine 2-cyclo-pentoxy-4- [N-methyl- (4-cyclo-pentoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-hexyloxy-4- [N-methyl- (4 -Cyclo-pentoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-cyclo-hexyloxy-4- [N-methyl- (4-cyclo-pentoxyphenyl) amino] -5- (trifluoro Methyl) pyrimidine and the like.
本発明の一般式(1)で表わされる2−アルコキシ−5−(トリフルオロメチル)ピリミジン誘導体でR1がn−ヘキシルオキシ基である化合物としては、具体的には例えば、2−メトキシ−4−[N−メチル−(2−n−ヘキシルオキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−エトキシ−4−[N−メチル−(2−n−ヘキシルオキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−プロポキシ−4−[N−メチル−(2−n−ヘキシルオキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−プロポキシ−4−[N−メチル−(2−n−ヘキシルオキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−iso−プロポキシ−4−[N−メチル−(2−n−ヘキシルオキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ブトキシ−4−[N−メチル−(2−n−ヘキシルオキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−iso−ブトキシ−4−[N−メチル−(2−n−ヘキシルオキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−sec−ブトキシ−4−[N−メチル−(2−n−ヘキシルオキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−tert−ブトキシ−4−[N−メチル−(2−n−ヘキシルオキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ペントキシ−4−[N−メチル−(2−n−ヘキシルオキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−cyclo−ペントキシ−4−[N−メチル−(2−n−ヘキシルオキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ヘキシルオキシ−4−[N−メチル−(2−n−ヘキシルオキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−cyclo−ヘキシルオキシ−4−[N−メチル−(2−n−ヘキシルオキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−メトキシ−4−[N−メチル−(3−n−ヘキシルオキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−エトキシ−4−[N−メチル−(3−n−ヘキシルオキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−プロポキシ−4−[N−メチル−(3−n−ヘキシルオキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−プロポキシ−4−[N−メチル−(3−n−ヘキシルオキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−iso−プロポキシ−4−[N−メチル−(3−n−ヘキシルオキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ブトキシ−4−[N−メチル−(3−n−ヘキシルオキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−iso−ブトキシ−4−[N−メチル−(3−n−ヘキシルオキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−sec−ブトキシ−4−[N−メチル−(3−n−ヘキシルオキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−tert−ブトキシ−4−[N−メチル−(3−n−ヘキシルオキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ペントキシ−4−[N−メチル−(3−n−ヘキシルオキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−cyclo−ペントキシ−4−[N−メチル−(3−n−ヘキシルオキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ヘキシルオキシ−4−[N−メチル−(3−n−ヘキシルオキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−cyclo−ヘキシルオキシ−4−[N−メチル−(3−n−ヘキシルオキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−メトキシ−4−[N−メチル−(4−n−ヘキシルオキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−エトキシ−4−[N−メチル−(4−n−ヘキシルオキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−プロポキシ−4−[N−メチル−(4−n−ヘキシルオキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−プロポキシ−4−[N−メチル−(4−n−ヘキシルオキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−iso−プロポキシ−4−[N−メチル−(4−n−ヘキシルオキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ブトキシ−4−[N−メチル−(4−n−ヘキシルオキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−iso−ブトキシ−4−[N−メチル−(4−n−ヘキシルオキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−sec−ブトキシ−4−[N−メチル−(4−n−ヘキシルオキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−tert−ブトキシ−4−[N−メチル−(4−n−ヘキシルオキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ペントキシ−4−[N−メチル−(4−n−ヘキシルオキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−cyclo−ペントキシ−4−[N−メチル−(4−n−ヘキシルオキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ヘキシルオキシ−4−[N−メチル−(4−n−ヘキシルオキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−cyclo−ヘキシルオキシ−4−[N−メチル−(4−n−ヘキシルオキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン等が挙げられる。 Specific examples of the 2-alkoxy-5- (trifluoromethyl) pyrimidine derivative represented by the general formula (1) of the present invention in which R 1 is an n-hexyloxy group include, for example, 2-methoxy-4 -[N-methyl- (2-n-hexyloxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-ethoxy-4- [N-methyl- (2-n-hexyloxyphenyl) amino]- 5- (trifluoromethyl) pyrimidine, 2-n-propoxy-4- [N-methyl- (2-n-hexyloxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-propoxy-4 -[N-methyl- (2-n-hexyloxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-iso-propoxy-4- [N-methyl (2-n-hexyloxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-butoxy-4- [N-methyl- (2-n-hexyloxyphenyl) amino] -5- (tri Fluoromethyl) pyrimidine, 2-iso-butoxy-4- [N-methyl- (2-n-hexyloxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-sec-butoxy-4- [N- Methyl- (2-n-hexyloxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-tert-butoxy-4- [N-methyl- (2-n-hexyloxyphenyl) amino] -5 (Trifluoromethyl) pyrimidine, 2-n-pentoxy-4- [N-methyl- (2-n-hexyloxyphenyl) amino] -5- (trifluoro Romethyl) pyrimidine, 2-cyclo-pentoxy-4- [N-methyl- (2-n-hexyloxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-hexyloxy-4- [N- Methyl- (2-n-hexyloxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-cyclo-hexyloxy-4- [N-methyl- (2-n-hexyloxyphenyl) amino] -5 -(Trifluoromethyl) pyrimidine, 2-methoxy-4- [N-methyl- (3-n-hexyloxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-ethoxy-4- [N-methyl -(3-n-hexyloxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-propoxy-4- [N-me Ru- (3-n-hexyloxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-propoxy-4- [N-methyl- (3-n-hexyloxyphenyl) amino] -5 (Trifluoromethyl) pyrimidine, 2-iso-propoxy-4- [N-methyl- (3-n-hexyloxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-butoxy-4- [ N-methyl- (3-n-hexyloxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-iso-butoxy-4- [N-methyl- (3-n-hexyloxyphenyl) amino]- 5- (trifluoromethyl) pyrimidine, 2-sec-butoxy-4- [N-methyl- (3-n-hexyloxyphenyl) amino] -5- (tri Fluoromethyl) pyrimidine, 2-tert-butoxy-4- [N-methyl- (3-n-hexyloxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-pentoxy-4- [N-methyl -(3-n-hexyloxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-cyclo-pentoxy-4- [N-methyl- (3-n-hexyloxyphenyl) amino] -5- ( Trifluoromethyl) pyrimidine, 2-n-hexyloxy-4- [N-methyl- (3-n-hexyloxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-cyclo-hexyloxy-4- [N-methyl- (3-n-hexyloxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-methoxy -4- [N-methyl- (4-n-hexyloxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-ethoxy-4- [N-methyl- (4-n-hexyloxyphenyl) amino ] -5- (trifluoromethyl) pyrimidine, 2-n-propoxy-4- [N-methyl- (4-n-hexyloxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-propoxy -4- [N-methyl- (4-n-hexyloxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-iso-propoxy-4- [N-methyl- (4-n-hexyloxyphenyl) ) Amino] -5- (trifluoromethyl) pyrimidine, 2-n-butoxy-4- [N-methyl- (4-n-hexyloxyphenyl) amino] -5- ( Trifluoromethyl) pyrimidine, 2-iso-butoxy-4- [N-methyl- (4-n-hexyloxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-sec-butoxy-4- [N -Methyl- (4-n-hexyloxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-tert-butoxy-4- [N-methyl- (4-n-hexyloxyphenyl) amino] -5 -(Trifluoromethyl) pyrimidine, 2-n-pentoxy-4- [N-methyl- (4-n-hexyloxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-cyclo-pentoxy-4- [N-methyl- (4-n-hexyloxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-hexylo Ci-4- [N-methyl- (4-n-hexyloxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-cyclo-hexyloxy-4- [N-methyl- (4-n-hexyl) Oxyphenyl) amino] -5- (trifluoromethyl) pyrimidine and the like.
本発明の一般式(1)で表わされる2−アルコキシ−5−(トリフルオロメチル)ピリミジン誘導体でR1がcyclo−ヘキシルオキシ基である化合物としては、具体的には例えば、2−メトキシ−4−[N−メチル−(2−cyclo−ヘキシルオキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−エトキシ−4−[N−メチル−(2−cyclo−ヘキシルオキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−プロポキシ−4−[N−メチル−(2−cyclo−ヘキシルオキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−プロポキシ−4−[N−メチル−(2−cyclo−ヘキシルオキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−iso−プロポキシ−4−[N−メチル−(2−cyclo−ヘキシルオキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ブトキシ−4−[N−メチル−(2−cyclo−ヘキシルオキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−iso−ブトキシ−4−[N−メチル−(2−cyclo−ヘキシルオキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−sec−ブトキシ−4−[N−メチル−(2−cyclo−ヘキシルオキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−tert−ブトキシ−4−[N−メチル−(2−cyclo−ヘキシルオキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ペントキシ−4−[N−メチル−(2−cyclo−ヘキシルオキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−cyclo−ペントキシ−4−[N−メチル−(2−cyclo−ヘキシルオキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ヘキシルオキシ−4−[N−メチル−(2−cyclo−ヘキシルオキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−cyclo−ヘキシルオキシ−4−[N−メチル−(2−cyclo−ヘキシルオキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−メトキシ−4−[N−メチル−(3−cyclo−ヘキシルオキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−エトキシ−4−[N−メチル−(3−cyclo−ヘキシルオキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−プロポキシ−4−[N−メチル−(3−cyclo−ヘキシルオキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−プロポキシ−4−[N−メチル−(3−cyclo−ヘキシルオキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−iso−プロポキシ−4−[N−メチル−(3−cyclo−ヘキシルオキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ブトキシ−4−[N−メチル−(3−cyclo−ヘキシルオキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−iso−ブトキシ−4−[N−メチル−(3−cyclo−ヘキシルオキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−sec−ブトキシ−4−[N−メチル−(3−cyclo−ヘキシルオキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−tert−ブトキシ−4−[N−メチル−(3−cyclo−ヘキシルオキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ペントキシ−4−[N−メチル−(3−cyclo−ヘキシルオキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−cyclo−ペントキシ−4−[N−メチル−(3−cyclo−ヘキシルオキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ヘキシルオキシ−4−[N−メチル−(3−cyclo−ヘキシルオキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−cyclo−ヘキシルオキシ−4−[N−メチル−(3−cyclo−ヘキシルオキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−メトキシ−4−[N−メチル−(4−cyclo−ヘキシルオキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−エトキシ−4−[N−メチル−(4−cyclo−ヘキシルオキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−プロポキシ−4−[N−メチル−(4−cyclo−ヘキシルオキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−プロポキシ−4−[N−メチル−(4−cyclo−ヘキシルオキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−iso−プロポキシ−4−[N−メチル−(4−cyclo−ヘキシルオキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ブトキシ−4−[N−メチル−(4−cyclo−ヘキシルオキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−iso−ブトキシ−4−[N−メチル−(4−cyclo−ヘキシルオキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−sec−ブトキシ−4−[N−メチル−(4−cyclo−ヘキシルオキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−tert−ブトキシ−4−[N−メチル−(4−cyclo−ヘキシルオキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ペントキシ−4−[N−メチル−(4−cyclo−ヘキシルオキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−cyclo−ペントキシ−4−[N−メチル−(4−cyclo−ヘキシルオキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ヘキシルオキシ−4−[N−メチル−(4−cyclo−ヘキシルオキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−cyclo−ヘキシルオキシ−4−[N−メチル−(4−cyclo−ヘキシルオキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン等が挙げられる。 Specific examples of the 2-alkoxy-5- (trifluoromethyl) pyrimidine derivative represented by the general formula (1) of the present invention in which R 1 is a cyclo-hexyloxy group include 2-methoxy-4 -[N-methyl- (2-cyclo-hexyloxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-ethoxy-4- [N-methyl- (2-cyclo-hexyloxyphenyl) amino]- 5- (trifluoromethyl) pyrimidine, 2-n-propoxy-4- [N-methyl- (2-cyclo-hexyloxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-propoxy-4 -[N-methyl- (2-cyclo-hexyloxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, -Iso-propoxy-4- [N-methyl- (2-cyclo-hexyloxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-butoxy-4- [N-methyl- (2-cyclo) -Hexyloxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-iso-butoxy-4- [N-methyl- (2-cyclo-hexyloxyphenyl) amino] -5- (trifluoromethyl) pyrimidine 2-sec-butoxy-4- [N-methyl- (2-cyclo-hexyloxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-tert-butoxy-4- [N-methyl- (2 -Cyclo-hexyloxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-pentoxy -4- [N-methyl- (2-cyclo-hexyloxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-cyclo-pentoxy-4- [N-methyl- (2-cyclo-hexyloxyphenyl) ) Amino] -5- (trifluoromethyl) pyrimidine, 2-n-hexyloxy-4- [N-methyl- (2-cyclo-hexyloxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2- cyclo-hexyloxy-4- [N-methyl- (2-cyclo-hexyloxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-methoxy-4- [N-methyl- (3-cyclo-hexyl) Oxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-ethoxy-4- [N-me Ru- (3-cyclo-hexyloxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-propoxy-4- [N-methyl- (3-cyclo-hexyloxyphenyl) amino] -5 (Trifluoromethyl) pyrimidine, 2-n-propoxy-4- [N-methyl- (3-cyclo-hexyloxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-iso-propoxy-4- [ N-methyl- (3-cyclo-hexyloxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-butoxy-4- [N-methyl- (3-cyclyl-hexyloxyphenyl) amino]- 5- (Trifluoromethyl) pyrimidine, 2-iso-butoxy-4- [N-methyl- (3-cyclo) Hexyloxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-sec-butoxy-4- [N-methyl- (3-cyclo-hexyloxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-tert-Butoxy-4- [N-methyl- (3-cyclo-hexyloxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-pentoxy-4- [N-methyl- (3- cyclo-hexyloxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-cyclo-pentoxy-4- [N-methyl- (3-cyclo-hexyloxyphenyl) amino] -5- (trifluoromethyl) Pyrimidine, 2-n-hexyloxy-4- [N-methyl- (3-cyclo-hexyl) Oxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-cyclo-hexyloxy-4- [N-methyl- (3-cyclo-hexyloxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-methoxy-4- [N-methyl- (4-cyclo-hexyloxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-ethoxy-4- [N-methyl- (4-cyclo-hexyloxy) Phenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-propoxy-4- [N-methyl- (4-cyclo-hexyloxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2- n-propoxy-4- [N-methyl- (4-cyclo-hexyloxyphenyl) amino]- -(Trifluoromethyl) pyrimidine, 2-iso-propoxy-4- [N-methyl- (4-cyclo-hexyloxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-butoxy-4- [N-methyl- (4-cyclo-hexyloxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-iso-butoxy-4- [N-methyl- (4-cyclo-hexyloxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-sec-butoxy-4- [N-methyl- (4-cyclo-hexyloxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-tert-butoxy- 4- [N-methyl- (4-cyclo-hexyloxyphenyl) amino] -5- (trifluoro Methyl) pyrimidine, 2-n-pentoxy-4- [N-methyl- (4-cyclo-hexyloxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-cyclo-pentoxy-4- [N-methyl] -(4-Cyclo-hexyloxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-hexyloxy-4- [N-methyl- (4-cyclooxy-hexyloxyphenyl) amino] -5 (Trifluoromethyl) pyrimidine, 2-cyclo-hexyloxy-4- [N-methyl- (4-cyclo-hexyloxyphenyl) amino] -5- (trifluoromethyl) pyrimidine and the like.
本発明の一般式(1)で表わされる2−アルコキシ−5−(トリフルオロメチル)ピリミジン誘導体でR1がフッ素原子である化合物としては、具体的には例えば、2−メトキシ−4−[N−メチル−(2−フルオロフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−エトキシ−4−[N−メチル−(2−フルオロフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−プロポキシ−4−[N−メチル−(2−フルオロフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−プロポキシ−4−[N−メチル−(2−フルオロフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−iso−プロポキシ−4−[N−メチル−(2−フルオロフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ブトキシ−4−[N−メチル−(2−フルオロフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−iso−ブトキシ−4−[N−メチル−(2−フルオロフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−sec−ブトキシ−4−[N−メチル−(2−フルオロフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−tert−ブトキシ−4−[N−メチル−(2−フルオロフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ペントキシ−4−[N−メチル−(2−フルオロフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−cyclo−ペントキシ−4−[N−メチル−(2−フルオロフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ヘキシルオキシ−4−[N−メチル−(2−フルオロフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−cyclo−ヘキシルオキシ−4−[N−メチル−(2−フルオロフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−メトキシ−4−[N−メチル−(3−フルオロフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−エトキシ−4−[N−メチル−(3−フルオロフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−プロポキシ−4−[N−メチル−(3−フルオロフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−プロポキシ−4−[N−メチル−(3−フルオロフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−iso−プロポキシ−4−[N−メチル−(3−フルオロフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ブトキシ−4−[N−メチル−(3−フルオロフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−iso−ブトキシ−4−[N−メチル−(3−フルオロフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−sec−ブトキシ−4−[N−メチル−(3−フルオロフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−tert−ブトキシ−4−[N−メチル−(3−フルオロフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ペントキシ−4−[N−メチル−(3−フルオロフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−cyclo−ペントキシ−4−[N−メチル−(3−フルオロフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ヘキシルオキシ−4−[N−メチル−(3−フルオロフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−cyclo−ヘキシルオキシ−4−[N−メチル−(3−フルオロフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−メトキシ−4−[N−メチル−(4−フルオロフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−エトキシ−4−[N−メチル−(4−フルオロフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−プロポキシ−4−[N−メチル−(4−フルオロフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−プロポキシ−4−[N−メチル−(4−フルオロフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−iso−プロポキシ−4−[N−メチル−(4−フルオロフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ブトキシ−4−[N−メチル−(4−フルオロフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−iso−ブトキシ−4−[N−メチル−(4−フルオロフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−sec−ブトキシ−4−[N−メチル−(4−フルオロフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−tert−ブトキシ−4−[N−メチル−(4−フルオロフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ペントキシ−4−[N−メチル−(4−フルオロフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−cyclo−ペントキシ−4−[N−メチル−(4−フルオロフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ヘキシルオキシ−4−[N−メチル−(4−フルオロフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−cyclo−ヘキシルオキシ−4−[N−メチル−(4−フルオロフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン等が挙げられる。 Specific examples of the 2-alkoxy-5- (trifluoromethyl) pyrimidine derivative represented by the general formula (1) of the present invention in which R 1 is a fluorine atom include 2-methoxy-4- [N -Methyl- (2-fluorophenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-ethoxy-4- [N-methyl- (2-fluorophenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-propoxy-4- [N-methyl- (2-fluorophenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-propoxy-4- [N-methyl- (2-fluorophenyl) Amino] -5- (trifluoromethyl) pyrimidine, 2-iso-propoxy-4- [N-methyl- (2-fluorophenyl) amino] -5- (trifluoro) Romethyl) pyrimidine, 2-n-butoxy-4- [N-methyl- (2-fluorophenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-iso-butoxy-4- [N-methyl- (2 -Fluorophenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-sec-butoxy-4- [N-methyl- (2-fluorophenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-tert -Butoxy-4- [N-methyl- (2-fluorophenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-pentoxy-4- [N-methyl- (2-fluorophenyl) amino]- 5- (trifluoromethyl) pyrimidine, 2-cyclo-pentoxy-4- [N-methyl- (2-fluorophenyl) amino] -5- (to (Rifluoromethyl) pyrimidine, 2-n-hexyloxy-4- [N-methyl- (2-fluorophenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-cyclo-hexyloxy-4- [N- Methyl- (2-fluorophenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-methoxy-4- [N-methyl- (3-fluorophenyl) amino] -5- (trifluoromethyl) pyrimidine, 2 -Ethoxy-4- [N-methyl- (3-fluorophenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-propoxy-4- [N-methyl- (3-fluorophenyl) amino]- 5- (trifluoromethyl) pyrimidine, 2-n-propoxy-4- [N-methyl- (3-fluorophenyl) amino] -5- (tri Fluoromethyl) pyrimidine, 2-iso-propoxy-4- [N-methyl- (3-fluorophenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-butoxy-4- [N-methyl- (3 -Fluorophenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-iso-butoxy-4- [N-methyl- (3-fluorophenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-sec -Butoxy-4- [N-methyl- (3-fluorophenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-tert-butoxy-4- [N-methyl- (3-fluorophenyl) amino]- 5- (trifluoromethyl) pyrimidine, 2-n-pentoxy-4- [N-methyl- (3-fluorophenyl) amino] -5- ( Trifluoromethyl) pyrimidine, 2-cyclo-pentoxy-4- [N-methyl- (3-fluorophenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-hexyloxy-4- [N-methyl -(3-Fluorophenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-cyclo-hexyloxy-4- [N-methyl- (3-fluorophenyl) amino] -5- (trifluoromethyl) pyrimidine 2-methoxy-4- [N-methyl- (4-fluorophenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-ethoxy-4- [N-methyl- (4-fluorophenyl) amino]- 5- (trifluoromethyl) pyrimidine, 2-n-propoxy-4- [N-methyl- (4-fluorophenyl) amino] -5 -(Trifluoromethyl) pyrimidine, 2-n-propoxy-4- [N-methyl- (4-fluorophenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-iso-propoxy-4- [N- Methyl- (4-fluorophenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-butoxy-4- [N-methyl- (4-fluorophenyl) amino] -5- (trifluoromethyl) pyrimidine 2-iso-butoxy-4- [N-methyl- (4-fluorophenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-sec-butoxy-4- [N-methyl- (4-fluorophenyl) ) Amino] -5- (trifluoromethyl) pyrimidine, 2-tert-butoxy-4- [N-methyl- (4-fluorophenyl) amino] 5- (trifluoromethyl) pyrimidine, 2-n-pentoxy-4- [N-methyl- (4-fluorophenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-cyclo-pentoxy-4- [N -Methyl- (4-fluorophenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-hexyloxy-4- [N-methyl- (4-fluorophenyl) amino] -5- (trifluoromethyl ) Pyrimidine, 2-cyclo-hexyloxy-4- [N-methyl- (4-fluorophenyl) amino] -5- (trifluoromethyl) pyrimidine and the like.
本発明の一般式(1)で表わされる2−アルコキシ−5−(トリフルオロメチル)ピリミジン誘導体でR1が塩素原子である化合物としては、具体的には例えば、2−メトキシ−4−[N−メチル−(2−クロロフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−エトキシ−4−[N−メチル−(2−クロロフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−プロポキシ−4−[N−メチル−(2−クロロフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−プロポキシ−4−[N−メチル−(2−クロロフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−iso−プロポキシ−4−[N−メチル−(2−クロロフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ブトキシ−4−[N−メチル−(2−クロロフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−iso−ブトキシ−4−[N−メチル−(2−クロロフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−sec−ブトキシ−4−[N−メチル−(2−クロロフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−tert−ブトキシ−4−[N−メチル−(2−クロロフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ペントキシ−4−[N−メチル−(2−クロロフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−cyclo−ペントキシ−4−[N−メチル−(2−クロロフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ヘキシルオキシ−4−[N−メチル−(2−クロロフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−cyclo−ヘキシルオキシ−4−[N−メチル−(2−クロロフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−メトキシ−4−[N−メチル−(3−クロロフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−エトキシ−4−[N−メチル−(3−クロロフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−プロポキシ−4−[N−メチル−(3−クロロフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−プロポキシ−4−[N−メチル−(3−クロロフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−iso−プロポキシ−4−[N−メチル−(3−クロロフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ブトキシ−4−[N−メチル−(3−クロロフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−iso−ブトキシ−4−[N−メチル−(3−クロロフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−sec−ブトキシ−4−[N−メチル−(3−クロロフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−tert−ブトキシ−4−[N−メチル−(3−クロロフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ペントキシ−4−[N−メチル−(3−クロロフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−cyclo−ペントキシ−4−[N−メチル−(3−クロロフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ヘキシルオキシ−4−[N−メチル−(3−クロロフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−cyclo−ヘキシルオキシ−4−[N−メチル−(3−クロロフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−メトキシ−4−[N−メチル−(4−クロロフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−エトキシ−4−[N−メチル−(4−クロロフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−プロポキシ−4−[N−メチル−(4−クロロフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−プロポキシ−4−[N−メチル−(4−クロロフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−iso−プロポキシ−4−[N−メチル−(4−クロロフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ブトキシ−4−[N−メチル−(4−クロロフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−iso−ブトキシ−4−[N−メチル−(4−クロロフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−sec−ブトキシ−4−[N−メチル−(4−クロロフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−tert−ブトキシ−4−[N−メチル−(4−クロロフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ペントキシ−4−[N−メチル−(4−クロロフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−cyclo−ペントキシ−4−[N−メチル−(4−クロロフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ヘキシルオキシ−4−[N−メチル−(4−クロロフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−cyclo−ヘキシルオキシ−4−[N−メチル−(4−クロロフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン等が挙げられる。 Specific examples of the 2-alkoxy-5- (trifluoromethyl) pyrimidine derivative represented by the general formula (1) of the present invention in which R 1 is a chlorine atom include 2-methoxy-4- [N -Methyl- (2-chlorophenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-ethoxy-4- [N-methyl- (2-chlorophenyl) amino] -5- (trifluoromethyl) pyrimidine, 2- n-propoxy-4- [N-methyl- (2-chlorophenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-propoxy-4- [N-methyl- (2-chlorophenyl) amino] -5 -(Trifluoromethyl) pyrimidine, 2-iso-propoxy-4- [N-methyl- (2-chlorophenyl) amino] -5- (trifluoromethyl) Limidine, 2-n-butoxy-4- [N-methyl- (2-chlorophenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-iso-butoxy-4- [N-methyl- (2-chlorophenyl) Amino] -5- (trifluoromethyl) pyrimidine, 2-sec-butoxy-4- [N-methyl- (2-chlorophenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-tert-butoxy-4- [N-methyl- (2-chlorophenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-pentoxy-4- [N-methyl- (2-chlorophenyl) amino] -5- (trifluoromethyl) Pyrimidine, 2-cyclo-pentoxy-4- [N-methyl- (2-chlorophenyl) amino] -5- (trifluoromethyl) pyrim Gin, 2-n-hexyloxy-4- [N-methyl- (2-chlorophenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-cyclo-hexyloxy-4- [N-methyl- (2- Chlorophenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-methoxy-4- [N-methyl- (3-chlorophenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-ethoxy-4- [N -Methyl- (3-chlorophenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-propoxy-4- [N-methyl- (3-chlorophenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-propoxy-4- [N-methyl- (3-chlorophenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-is -Propoxy-4- [N-methyl- (3-chlorophenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-butoxy-4- [N-methyl- (3-chlorophenyl) amino] -5 (Trifluoromethyl) pyrimidine, 2-iso-butoxy-4- [N-methyl- (3-chlorophenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-sec-butoxy-4- [N-methyl- (3-chlorophenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-tert-butoxy-4- [N-methyl- (3-chlorophenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n -Pentoxy-4- [N-methyl- (3-chlorophenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-cyclo- Totoxy-4- [N-methyl- (3-chlorophenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-hexyloxy-4- [N-methyl- (3-chlorophenyl) amino] -5 (Trifluoromethyl) pyrimidine, 2-cyclo-hexyloxy-4- [N-methyl- (3-chlorophenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-methoxy-4- [N-methyl- ( 4-chlorophenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-ethoxy-4- [N-methyl- (4-chlorophenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-propoxy- 4- [N-methyl- (4-chlorophenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-propoxy-4- [N-methyl- (4-chlorophenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-iso-propoxy-4- [N-methyl- (4-chlorophenyl) amino] -5- (trifluoromethyl) Pyrimidine, 2-n-butoxy-4- [N-methyl- (4-chlorophenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-iso-butoxy-4- [N-methyl- (4-chlorophenyl) Amino] -5- (trifluoromethyl) pyrimidine, 2-sec-butoxy-4- [N-methyl- (4-chlorophenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-tert-butoxy-4- [N-methyl- (4-chlorophenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-pentoxy-4- [N-mes Ru- (4-chlorophenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-cyclo-pentoxy-4- [N-methyl- (4-chlorophenyl) amino] -5- (trifluoromethyl) pyrimidine, 2 -N-hexyloxy-4- [N-methyl- (4-chlorophenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-cyclo-hexyloxy-4- [N-methyl- (4-chlorophenyl) amino ] -5- (trifluoromethyl) pyrimidine and the like.
本発明の一般式(1)で表わされる2−アルコキシ−5−(トリフルオロメチル)ピリミジン誘導体でR1が臭素原子である化合物としては、具体的には例えば、2−メトキシ−4−[N−メチル−(2−ブロモフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−エトキシ−4−[N−メチル−(2−ブロモフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−プロポキシ−4−[N−メチル−(2−ブロモフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−プロポキシ−4−[N−メチル−(2−ブロモフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−iso−プロポキシ−4−[N−メチル−(2−ブロモフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ブトキシ−4−[N−メチル−(2−ブロモフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−iso−ブトキシ−4−[N−メチル−(2−ブロモフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−sec−ブトキシ−4−[N−メチル−(2−ブロモフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−tert−ブトキシ−4−[N−メチル−(2−ブロモフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ペントキシ−4−[N−メチル−(2−ブロモフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−cyclo−ペントキシ−4−[N−メチル−(2−ブロモフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ヘキシルオキシ−4−[N−メチル−(2−ブロモフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−cyclo−ヘキシルオキシ−4−[N−メチル−(2−ブロモフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−メトキシ−4−[N−メチル−(3−ブロモフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−エトキシ−4−[N−メチル−(3−ブロモフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−プロポキシ−4−[N−メチル−(3−ブロモフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−プロポキシ−4−[N−メチル−(3−ブロモフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−iso−プロポキシ−4−[N−メチル−(3−ブロモフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ブトキシ−4−[N−メチル−(3−ブロモフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−iso−ブトキシ−4−[N−メチル−(3−ブロモフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−sec−ブトキシ−4−[N−メチル−(3−ブロモフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−tert−ブトキシ−4−[N−メチル−(3−ブロモフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ペントキシ−4−[N−メチル−(3−ブロモフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−cyclo−ペントキシ−4−[N−メチル−(3−ブロモフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ヘキシルオキシ−4−[N−メチル−(3−ブロモフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−cyclo−ヘキシルオキシ−4−[N−メチル−(3−ブロモフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−メトキシ−4−[N−メチル−(4−ブロモフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−エトキシ−4−[N−メチル−(4−ブロモフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−プロポキシ−4−[N−メチル−(4−ブロモフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−プロポキシ−4−[N−メチル−(4−ブロモフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−iso−プロポキシ−4−[N−メチル−(4−ブロモフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ブトキシ−4−[N−メチル−(4−ブロモフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−iso−ブトキシ−4−[N−メチル−(4−ブロモフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−sec−ブトキシ−4−[N−メチル−(4−ブロモフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−tert−ブトキシ−4−[N−メチル−(4−ブロモフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ペントキシ−4−[N−メチル−(4−ブロモフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−cyclo−ペントキシ−4−[N−メチル−(4−ブロモフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ヘキシルオキシ−4−[N−メチル−(4−ブロモフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−cyclo−ヘキシルオキシ−4−[N−メチル−(4−ブロモフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン等が挙げられる。 Specific examples of the 2-alkoxy-5- (trifluoromethyl) pyrimidine derivative represented by the general formula (1) of the present invention in which R 1 is a bromine atom include 2-methoxy-4- [N -Methyl- (2-bromophenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-ethoxy-4- [N-methyl- (2-bromophenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-propoxy-4- [N-methyl- (2-bromophenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-propoxy-4- [N-methyl- (2-bromophenyl) Amino] -5- (trifluoromethyl) pyrimidine, 2-iso-propoxy-4- [N-methyl- (2-bromophenyl) amino] -5- (trifluoromethyl) Limidine, 2-n-butoxy-4- [N-methyl- (2-bromophenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-iso-butoxy-4- [N-methyl- (2-bromo Phenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-sec-butoxy-4- [N-methyl- (2-bromophenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-tert-butoxy -4- [N-methyl- (2-bromophenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-pentoxy-4- [N-methyl- (2-bromophenyl) amino] -5 (Trifluoromethyl) pyrimidine, 2-cyclo-pentoxy-4- [N-methyl- (2-bromophenyl) amino] -5- (trifluoromethyl) pyrim Gin, 2-n-hexyloxy-4- [N-methyl- (2-bromophenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-cyclo-hexyloxy-4- [N-methyl- (2 -Bromophenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-methoxy-4- [N-methyl- (3-bromophenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-ethoxy-4 -[N-methyl- (3-bromophenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-propoxy-4- [N-methyl- (3-bromophenyl) amino] -5- (tri Fluoromethyl) pyrimidine, 2-n-propoxy-4- [N-methyl- (3-bromophenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-is -Propoxy-4- [N-methyl- (3-bromophenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-butoxy-4- [N-methyl- (3-bromophenyl) amino]- 5- (trifluoromethyl) pyrimidine, 2-iso-butoxy-4- [N-methyl- (3-bromophenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-sec-butoxy-4- [N -Methyl- (3-bromophenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-tert-butoxy-4- [N-methyl- (3-bromophenyl) amino] -5- (trifluoromethyl) Pyrimidine, 2-n-pentoxy-4- [N-methyl- (3-bromophenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-cyclo- Totoxy-4- [N-methyl- (3-bromophenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-hexyloxy-4- [N-methyl- (3-bromophenyl) amino]- 5- (trifluoromethyl) pyrimidine, 2-cyclo-hexyloxy-4- [N-methyl- (3-bromophenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-methoxy-4- [N- Methyl- (4-bromophenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-ethoxy-4- [N-methyl- (4-bromophenyl) amino] -5- (trifluoromethyl) pyrimidine, 2 -N-propoxy-4- [N-methyl- (4-bromophenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-propoxy-4- [N-methyl- (4-bromophenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-iso-propoxy-4- [N-methyl- (4-bromophenyl) amino] -5- (trifluoro Methyl) pyrimidine, 2-n-butoxy-4- [N-methyl- (4-bromophenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-iso-butoxy-4- [N-methyl- (4 -Bromophenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-sec-butoxy-4- [N-methyl- (4-bromophenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-tert -Butoxy-4- [N-methyl- (4-bromophenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-pentoxy-4- [N-me Ru- (4-bromophenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-cyclo-pentoxy-4- [N-methyl- (4-bromophenyl) amino] -5- (trifluoromethyl) pyrimidine 2-n-hexyloxy-4- [N-methyl- (4-bromophenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-cyclo-hexyloxy-4- [N-methyl- (4- Bromophenyl) amino] -5- (trifluoromethyl) pyrimidine and the like.
本発明の一般式(1)で表わされる2−アルコキシ−5−(トリフルオロメチル)ピリミジン誘導体でR1がヨウ素原子である化合物としては、具体的には例えば、2−メトキシ−4−[N−メチル−(2−ヨードフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−エトキシ−4−[N−メチル−(2−ヨードフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−プロポキシ−4−[N−メチル−(2−ヨードフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−プロポキシ−4−[N−メチル−(2−ヨードフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−iso−プロポキシ−4−[N−メチル−(2−ヨードフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ブトキシ−4−[N−メチル−(2−ヨードフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−iso−ブトキシ−4−[N−メチル−(2−ヨードフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−sec−ブトキシ−4−[N−メチル−(2−ヨードフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−tert−ブトキシ−4−[N−メチル−(2−ヨードフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ペントキシ−4−[N−メチル−(2−ヨードフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−cyclo−ペントキシ−4−[N−メチル−(2−ヨードフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ヘキシルオキシ−4−[N−メチル−(2−ヨードフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−cyclo−ヘキシルオキシ−4−[N−メチル−(2−ヨードフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−メトキシ−4−[N−メチル−(3−ヨードフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−エトキシ−4−[N−メチル−(3−ヨードフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−プロポキシ−4−[N−メチル−(3−ヨードフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−プロポキシ−4−[N−メチル−(3−ヨードフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−iso−プロポキシ−4−[N−メチル−(3−ヨードフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ブトキシ−4−[N−メチル−(3−ヨードフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−iso−ブトキシ−4−[N−メチル−(3−ヨードフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−sec−ブトキシ−4−[N−メチル−(3−ヨードフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−tert−ブトキシ−4−[N−メチル−(3−ヨードフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ペントキシ−4−[N−メチル−(3−ヨードフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−cyclo−ペントキシ−4−[N−メチル−(3−ヨードフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ヘキシルオキシ−4−[N−メチル−(3−ヨードフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−cyclo−ヘキシルオキシ−4−[N−メチル−(3−ヨードフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−メトキシ−4−[N−メチル−(4−ヨードフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−エトキシ−4−[N−メチル−(4−ヨードフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−プロポキシ−4−[N−メチル−(4−ヨードフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−プロポキシ−4−[N−メチル−(4−ヨードフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−iso−プロポキシ−4−[N−メチル−(4−ヨードフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ブトキシ−4−[N−メチル−(4−ヨードフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−iso−ブトキシ−4−[N−メチル−(4−ヨードフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−sec−ブトキシ−4−[N−メチル−(4−ヨードフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−tert−ブトキシ−4−[N−メチル−(4−ヨードフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ペントキシ−4−[N−メチル−(4−ヨードフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−cyclo−ペントキシ−4−[N−メチル−(4−ヨードフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ヘキシルオキシ−4−[N−メチル−(4−ヨードフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−cyclo−ヘキシルオキシ−4−[N−メチル−(4−ヨードフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン等が挙げられる。 Specific examples of the 2-alkoxy-5- (trifluoromethyl) pyrimidine derivative represented by the general formula (1) of the present invention in which R 1 is an iodine atom include 2-methoxy-4- [N -Methyl- (2-iodophenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-ethoxy-4- [N-methyl- (2-iodophenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-propoxy-4- [N-methyl- (2-iodophenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-propoxy-4- [N-methyl- (2-iodophenyl) Amino] -5- (trifluoromethyl) pyrimidine, 2-iso-propoxy-4- [N-methyl- (2-iodophenyl) amino] -5- (trifluoromethyl) Pyrimidine, 2-n-butoxy-4- [N-methyl- (2-iodophenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-iso-butoxy-4- [N-methyl- (2-iodo) Phenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-sec-butoxy-4- [N-methyl- (2-iodophenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-tert-butoxy -4- [N-methyl- (2-iodophenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-pentoxy-4- [N-methyl- (2-iodophenyl) amino] -5 (Trifluoromethyl) pyrimidine, 2-cyclo-pentoxy-4- [N-methyl- (2-iodophenyl) amino] -5- (trifluoromethyl) pyri Midine, 2-n-hexyloxy-4- [N-methyl- (2-iodophenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-cyclo-hexyloxy-4- [N-methyl- (2 -Iodophenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-methoxy-4- [N-methyl- (3-iodophenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-ethoxy-4 -[N-methyl- (3-iodophenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-propoxy-4- [N-methyl- (3-iodophenyl) amino] -5- (tri Fluoromethyl) pyrimidine, 2-n-propoxy-4- [N-methyl- (3-iodophenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-i o-propoxy-4- [N-methyl- (3-iodophenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-butoxy-4- [N-methyl- (3-iodophenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-iso-butoxy-4- [N-methyl- (3-iodophenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-sec-butoxy-4- [ N-methyl- (3-iodophenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-tert-butoxy-4- [N-methyl- (3-iodophenyl) amino] -5- (trifluoromethyl ) Pyrimidine, 2-n-pentoxy-4- [N-methyl- (3-iodophenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-cyclo Pentoxy-4- [N-methyl- (3-iodophenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-hexyloxy-4- [N-methyl- (3-iodophenyl) amino]- 5- (trifluoromethyl) pyrimidine, 2-cyclo-hexyloxy-4- [N-methyl- (3-iodophenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-methoxy-4- [N- Methyl- (4-iodophenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-ethoxy-4- [N-methyl- (4-iodophenyl) amino] -5- (trifluoromethyl) pyrimidine, 2 -N-propoxy-4- [N-methyl- (4-iodophenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-propoxy-4 -[N-methyl- (4-iodophenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-iso-propoxy-4- [N-methyl- (4-iodophenyl) amino] -5- (tri Fluoromethyl) pyrimidine, 2-n-butoxy-4- [N-methyl- (4-iodophenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-iso-butoxy-4- [N-methyl- ( 4-iodophenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-sec-butoxy-4- [N-methyl- (4-iodophenyl) amino] -5- (trifluoromethyl) pyrimidine, 2- tert-Butoxy-4- [N-methyl- (4-iodophenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-pentoxy-4- [N- Tyl- (4-iodophenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-cyclo-pentoxy-4- [N-methyl- (4-iodophenyl) amino] -5- (trifluoromethyl) pyrimidine 2-n-hexyloxy-4- [N-methyl- (4-iodophenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-cyclo-hexyloxy-4- [N-methyl- (4- Iodophenyl) amino] -5- (trifluoromethyl) pyrimidine and the like.
本発明の一般式(1)で表わされる2−アルコキシ−5−(トリフルオロメチル)ピリミジン誘導体でR1がシアノ基である化合物としては、具体的には例えば、2−メトキシ−4−[N−メチル−(2−シアノフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−エトキシ−4−[N−メチル−(2−シアノフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−プロポキシ−4−[N−メチル−(2−シアノフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−プロポキシ−4−[N−メチル−(2−シアノフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−iso−プロポキシ−4−[N−メチル−(2−シアノフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ブトキシ−4−[N−メチル−(2−シアノフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−iso−ブトキシ−4−[N−メチル−(2−シアノフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−sec−ブトキシ−4−[N−メチル−(2−シアノフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−tert−ブトキシ−4−[N−メチル−(2−シアノフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ペントキシ−4−[N−メチル−(2−シアノフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−cyclo−ペントキシ−4−[N−メチル−(2−シアノフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ヘキシルオキシ−4−[N−メチル−(2−シアノフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−cyclo−ヘキシルオキシ−4−[N−メチル−(2−シアノフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−メトキシ−4−[N−メチル−(3−シアノフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−エトキシ−4−[N−メチル−(3−シアノフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−プロポキシ−4−[N−メチル−(3−シアノフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−プロポキシ−4−[N−メチル−(3−シアノフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−iso−プロポキシ−4−[N−メチル−(3−シアノフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ブトキシ−4−[N−メチル−(3−シアノフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−iso−ブトキシ−4−[N−メチル−(3−シアノフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−sec−ブトキシ−4−[N−メチル−(3−シアノフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−tert−ブトキシ−4−[N−メチル−(3−シアノフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ペントキシ−4−[N−メチル−(3−シアノフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−cyclo−ペントキシ−4−[N−メチル−(3−シアノフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ヘキシルオキシ−4−[N−メチル−(3−シアノフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−cyclo−ヘキシルオキシ−4−[N−メチル−(3−シアノフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−メトキシ−4−[N−メチル−(4−シアノフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−エトキシ−4−[N−メチル−(4−シアノフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−プロポキシ−4−[N−メチル−(4−シアノフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−プロポキシ−4−[N−メチル−(4−シアノフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−iso−プロポキシ−4−[N−メチル−(4−シアノフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ブトキシ−4−[N−メチル−(4−シアノフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−iso−ブトキシ−4−[N−メチル−(4−シアノフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−sec−ブトキシ−4−[N−メチル−(4−シアノフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−tert−ブトキシ−4−[N−メチル−(4−シアノフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ペントキシ−4−[N−メチル−(4−シアノフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−cyclo−ペントキシ−4−[N−メチル−(4−シアノフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−n−ヘキシルオキシ−4−[N−メチル−(4−シアノフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−cyclo−ヘキシルオキシ−4−[N−メチル−(4−シアノフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン等が挙げられる。 Specific examples of the 2-alkoxy-5- (trifluoromethyl) pyrimidine derivative represented by the general formula (1) of the present invention in which R 1 is a cyano group include, for example, 2-methoxy-4- [N -Methyl- (2-cyanophenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-ethoxy-4- [N-methyl- (2-cyanophenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-propoxy-4- [N-methyl- (2-cyanophenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-propoxy-4- [N-methyl- (2-cyanophenyl) Amino] -5- (trifluoromethyl) pyrimidine, 2-iso-propoxy-4- [N-methyl- (2-cyanophenyl) amino] -5- (trifluoromethyl) Limidine, 2-n-butoxy-4- [N-methyl- (2-cyanophenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-iso-butoxy-4- [N-methyl- (2-cyano) Phenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-sec-butoxy-4- [N-methyl- (2-cyanophenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-tert-butoxy -4- [N-methyl- (2-cyanophenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-pentoxy-4- [N-methyl- (2-cyanophenyl) amino] -5 (Trifluoromethyl) pyrimidine, 2-cyclo-pentoxy-4- [N-methyl- (2-cyanophenyl) amino] -5- (trifluoromethyl) pyrim Gin, 2-n-hexyloxy-4- [N-methyl- (2-cyanophenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-cyclo-hexyloxy-4- [N-methyl- (2 -Cyanophenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-methoxy-4- [N-methyl- (3-cyanophenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-ethoxy-4 -[N-methyl- (3-cyanophenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-propoxy-4- [N-methyl- (3-cyanophenyl) amino] -5- (tri Fluoromethyl) pyrimidine, 2-n-propoxy-4- [N-methyl- (3-cyanophenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-is -Propoxy-4- [N-methyl- (3-cyanophenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-butoxy-4- [N-methyl- (3-cyanophenyl) amino]- 5- (trifluoromethyl) pyrimidine, 2-iso-butoxy-4- [N-methyl- (3-cyanophenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-sec-butoxy-4- [N -Methyl- (3-cyanophenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-tert-butoxy-4- [N-methyl- (3-cyanophenyl) amino] -5- (trifluoromethyl) Pyrimidine, 2-n-pentoxy-4- [N-methyl- (3-cyanophenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-cyclo- Totoxy-4- [N-methyl- (3-cyanophenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-hexyloxy-4- [N-methyl- (3-cyanophenyl) amino]- 5- (trifluoromethyl) pyrimidine, 2-cyclo-hexyloxy-4- [N-methyl- (3-cyanophenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-methoxy-4- [N- Methyl- (4-cyanophenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-ethoxy-4- [N-methyl- (4-cyanophenyl) amino] -5- (trifluoromethyl) pyrimidine, 2 -N-propoxy-4- [N-methyl- (4-cyanophenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-propoxy-4- [N-methyl- (4-cyanophenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-iso-propoxy-4- [N-methyl- (4-cyanophenyl) amino] -5- (trifluoro Methyl) pyrimidine, 2-n-butoxy-4- [N-methyl- (4-cyanophenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-iso-butoxy-4- [N-methyl- (4 -Cyanophenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-sec-butoxy-4- [N-methyl- (4-cyanophenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-tert -Butoxy-4- [N-methyl- (4-cyanophenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-n-pentoxy-4- [N-me Ru- (4-cyanophenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-cyclo-pentoxy-4- [N-methyl- (4-cyanophenyl) amino] -5- (trifluoromethyl) pyrimidine 2-n-hexyloxy-4- [N-methyl- (4-cyanophenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-cyclo-hexyloxy-4- [N-methyl- (4- Cyanophenyl) amino] -5- (trifluoromethyl) pyrimidine and the like.
本発明において、これらの一般式(1)で表わされる2−アルコキシ−5−(トリフルオロメチル)ピリミジン誘導体の内でも、R1が水素原子、メチル基又はエチル基である化合物が好適である。
本発明の一般式(2)で表わされる2−ベンジルオキシ−5−(トリフルオロメチル)ピリミジン誘導体でR1が水素原子、メチル基、エチル基又は炭素数3〜6の直鎖若しくは分岐若しくは環式のアルキルである化合物としては、具体的には例えば、2−ベンジルオキシ−4−(N−メチルフェニルアミノ)−5−(トリフルオロメチル)ピリミジン、2−ベンジルオキシ−4−[N−メチル−(2−メチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−ベンジルオキシ−4−[N−メチル−(3−メチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−ベンジルオキシ−4−[N−メチル−(4−メチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−ベンジルオキシ−4−[N−メチル−(2−エチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−ベンジルオキシ−4−[N−メチル−(3−エチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−ベンジルオキシ−4−[N−メチル−(4−エチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−ベンジルオキシ−4−[N−メチル−(2−n−プロピルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−ベンジルオキシ−4−[N−メチル−(3−n−プロピルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−ベンジルオキシ−4−[N−メチル−(4−n−プロピルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−ベンジルオキシ−4−[N−メチル−(2−iso−プロピルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−ベンジルオキシ−4−[N−メチル−(3−iso−プロピルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−ベンジルオキシ−4−[N−メチル−(4−iso−プロピルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−ベンジルオキシ−4−[N−メチル−(2−n−ブチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−ベンジルオキシ−4−[N−メチル−(3−n−ブチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−ベンジルオキシ−4−[N−メチル−(4−n−ブチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−ベンジルオキシ−4−[N−メチル−(2−iso−ブチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−ベンジルオキシ−4−[N−メチル−(3−iso−ブチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−ベンジルオキシ−4−[N−メチル−(4−iso−ブチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−ベンジルオキシ−4−[N−メチル−(2−sec−ブチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−ベンジルオキシ−4−[N−メチル−(3−sec−ブチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−ベンジルオキシ−4−[N−メチル−(4−sec−ブチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−ベンジルオキシ−4−[N−メチル−(2−tert−ブチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−ベンジルオキシ−4−[N−メチル−(3−tert−ブチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−ベンジルオキシ−4−[N−メチル−(4−tert−ブチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−ベンジルオキシ−4−[N−メチル−(2−n−ペンチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−ベンジルオキシ−4−[N−メチル−(3−n−ペンチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−ベンジルオキシ−4−[N−メチル−(4−n−ペンチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−ベンジルオキシ−4−[N−メチル−(2−cyclo−ペンチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−ベンジルオキシ−4−[N−メチル−(3−cyclo−ペンチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−ベンジルオキシ−4−[N−メチル−(4−cyclo−ペンチルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−ベンジルオキシ−4−[N−メチル−(2−n−ヘキシルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−ベンジルオキシ−4−[N−メチル−(3−n−ヘキシルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−ベンジルオキシ−4−[N−メチル−(4−n−ヘキシルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−ベンジルオキシ−4−[N−メチル−(2−cyclo−ヘキシルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−ベンジルオキシ−4−[N−メチル−(3−cyclo−ヘキシルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−ベンジルオキシ−4−[N−メチル−(4−cyclo−ヘキシルフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン等が挙げられる。
In the present invention, among the 2-alkoxy-5- (trifluoromethyl) pyrimidine derivatives represented by the general formula (1), compounds in which R 1 is a hydrogen atom, a methyl group or an ethyl group are preferable.
A 2-benzyloxy-5- (trifluoromethyl) pyrimidine derivative represented by the general formula (2) of the present invention, wherein R 1 is a hydrogen atom, a methyl group, an ethyl group, or a linear, branched or ring having 3 to 6 carbon atoms. Specific examples of the compound which is alkyl of the formula include 2-benzyloxy-4- (N-methylphenylamino) -5- (trifluoromethyl) pyrimidine, 2-benzyloxy-4- [N-methyl -(2-methylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-benzyloxy-4- [N-methyl- (3-methylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2 -Benzyloxy-4- [N-methyl- (4-methylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-benzyloxy-4- N-methyl- (2-ethylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-benzyloxy-4- [N-methyl- (3-ethylphenyl) amino] -5- (trifluoromethyl) Pyrimidine, 2-benzyloxy-4- [N-methyl- (4-ethylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-benzyloxy-4- [N-methyl- (2-n-propyl) Phenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-benzyloxy-4- [N-methyl- (3-n-propylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-benzyloxy -4- [N-methyl- (4-n-propylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-benzyloxy-4- [ N-methyl- (2-iso-propylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-benzyloxy-4- [N-methyl- (3-iso-propylphenyl) amino] -5- ( Trifluoromethyl) pyrimidine, 2-benzyloxy-4- [N-methyl- (4-iso-propylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-benzyloxy-4- [N-methyl- (2-n-Butylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-benzyloxy-4- [N-methyl- (3-n-butylphenyl) amino] -5- (trifluoromethyl) Pyrimidine, 2-benzyloxy-4- [N-methyl- (4-n-butylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2 Benzyloxy-4- [N-methyl- (2-iso-butylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-benzyloxy-4- [N-methyl- (3-iso-butylphenyl) Amino] -5- (trifluoromethyl) pyrimidine, 2-benzyloxy-4- [N-methyl- (4-iso-butylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-benzyloxy-4 -[N-methyl- (2-sec-butylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-benzyloxy-4- [N-methyl- (3-sec-butylphenyl) amino] -5 -(Trifluoromethyl) pyrimidine, 2-benzyloxy-4- [N-methyl- (4-sec-butylphenyl) amino] -5- (tri Fluoromethyl) pyrimidine, 2-benzyloxy-4- [N-methyl- (2-tert-butylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-benzyloxy-4- [N-methyl- (3 -Tert-butylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-benzyloxy-4- [N-methyl- (4-tert-butylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-Benzyloxy-4- [N-methyl- (2-n-pentylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-benzyloxy-4- [N-methyl- (3-n-pentyl) Phenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-benzyloxy-4- [N-methyl- (4-n-pentylph) Enyl) amino] -5- (trifluoromethyl) pyrimidine, 2-benzyloxy-4- [N-methyl- (2-cyclo-pentylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-benzyloxy -4- [N-methyl- (3-cyclo-pentylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-benzyloxy-4- [N-methyl- (4-cyclo-pentylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-benzyloxy-4- [N-methyl- (2-n-hexylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-benzyloxy-4- [ N-methyl- (3-n-hexylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-benzyloxy -4- [N-methyl- (4-n-hexylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-benzyloxy-4- [N-methyl- (2-cyclo-hexylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-benzyloxy-4- [N-methyl- (3-cyclo-hexylphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-benzyloxy-4- [ N-methyl- (4-cyclo-hexylphenyl) amino] -5- (trifluoromethyl) pyrimidine and the like.
本発明の一般式(2)で表わされる2−ベンジルオキシ−5−(トリフルオロメチル)ピリミジン誘導体でR1がメトキシ基、エトキシ基又は炭素数3〜6の直鎖若しくは分岐若しくは環式のアルコキシ基である化合物としては、具体的には例えば、2−ベンジルオキシ−4−[N−メチル−(2−メトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−ベンジルオキシ−4−[N−メチル−(3−メトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−ベンジルオキシ−4−[N−メチル−(4−メトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−ベンジルオキシ−4−[N−メチル−(2−エトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−ベンジルオキシ−4−[N−メチル−(3−エトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−ベンジルオキシ−4−[N−メチル−(4−エトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−ベンジルオキシ−4−[N−メチル−(2−n−プロポキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−ベンジルオキシ−4−[N−メチル−(3−n−プロポキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−ベンジルオキシ−4−[N−メチル−(4−n−プロポキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−ベンジルオキシ−4−[N−メチル−(2−iso−プロポキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−ベンジルオキシ−4−[N−メチル−(3−iso−プロポキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−ベンジルオキシ−4−[N−メチル−(4−iso−プロポキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−ベンジルオキシ−4−[N−メチル−(2−n−ブトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−ベンジルオキシ−4−[N−メチル−(3−n−ブトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−ベンジルオキシ−4−[N−メチル−(4−n−ブトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−ベンジルオキシ−4−[N−メチル−(2−iso−ブトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−ベンジルオキシ−4−[N−メチル−(3−iso−ブトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−ベンジルオキシ−4−[N−メチル−(4−iso−ブトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−ベンジルオキシ−4−[N−メチル−(2−sec−ブトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−ベンジルオキシ−4−[N−メチル−(3−sec−ブトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−ベンジルオキシ−4−[N−メチル−(4−sec−ブトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−ベンジルオキシ−4−[N−メチル−(2−tert−ブトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−ベンジルオキシ−4−[N−メチル−(4−tert−ブトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−ベンジルオキシ−4−[N−メチル−(4−tert−ブトキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−ベンジルオキシ−4−[N−メチル−(2−n−ペントキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−ベンジルオキシ−4−[N−メチル−(3−n−ペントキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−ベンジルオキシ−4−[N−メチル−(4−n−ペントキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−ベンジルオキシ−4−[N−メチル−(2−cyclo−ペントキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−ベンジルオキシ−4−[N−メチル−(3−cyclo−ペントキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−ベンジルオキシ−4−[N−メチル−(4−cyclo−ペントキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−ベンジルオキシ−4−[N−メチル−(2−n−ヘキシルオキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−ベンジルオキシ−4−[N−メチル−(3−n−ヘキシルオキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−ベンジルオキシ−4−[N−メチル−(4−n−ヘキシルオキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−ベンジルオキシ−4−[N−メチル−(2−cyclo−ヘキシルオキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−ベンジルオキシ−4−[N−メチル−(3−cyclo−ヘキシルオキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−ベンジルオキシ−4−[N−メチル−(4−cyclo−ヘキシルオキシフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン等が挙げられる。 A 2-benzyloxy-5- (trifluoromethyl) pyrimidine derivative represented by the general formula (2) of the present invention, in which R 1 is a methoxy group, an ethoxy group, or a linear, branched or cyclic alkoxy having 3 to 6 carbon atoms Specific examples of the compound as a group include 2-benzyloxy-4- [N-methyl- (2-methoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-benzyloxy-4- [N-methyl- (3-methoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-benzyloxy-4- [N-methyl- (4-methoxyphenyl) amino] -5- (trifluoromethyl ) Pyrimidine, 2-benzyloxy-4- [N-methyl- (2-ethoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2 Benzyloxy-4- [N-methyl- (3-ethoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-benzyloxy-4- [N-methyl- (4-ethoxyphenyl) amino] -5 -(Trifluoromethyl) pyrimidine, 2-benzyloxy-4- [N-methyl- (2-n-propoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-benzyloxy-4- [N- Methyl- (3-n-propoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-benzyloxy-4- [N-methyl- (4-n-propoxyphenyl) amino] -5- (trifluoro Methyl) pyrimidine, 2-benzyloxy-4- [N-methyl- (2-iso-propoxyphenyl) amino] -5- (trifluorome Til) pyrimidine, 2-benzyloxy-4- [N-methyl- (3-iso-propoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-benzyloxy-4- [N-methyl- (4 -Iso-propoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-benzyloxy-4- [N-methyl- (2-n-butoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-Benzyloxy-4- [N-methyl- (3-n-butoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-benzyloxy-4- [N-methyl- (4-n-butoxy) Phenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-benzyloxy-4- [N-methyl- (2-iso-butoxypheny) ) Amino] -5- (trifluoromethyl) pyrimidine, 2-benzyloxy-4- [N-methyl- (3-iso-butoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-benzyloxy- 4- [N-methyl- (4-iso-butoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-benzyloxy-4- [N-methyl- (2-sec-butoxyphenyl) amino]- 5- (trifluoromethyl) pyrimidine, 2-benzyloxy-4- [N-methyl- (3-sec-butoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-benzyloxy-4- [N -Methyl- (4-sec-butoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-benzyloxy-4- N-methyl- (2-tert-butoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-benzyloxy-4- [N-methyl- (4-tert-butoxyphenyl) amino] -5- ( Trifluoromethyl) pyrimidine, 2-benzyloxy-4- [N-methyl- (4-tert-butoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-benzyloxy-4- [N-methyl- (2-n-pentoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-benzyloxy-4- [N-methyl- (3-n-pentoxyphenyl) amino] -5- (trifluoro Methyl) pyrimidine, 2-benzyloxy-4- [N-methyl- (4-n-pentoxyphenyl) amino] -5- (trifluoromethyl) L) pyrimidine, 2-benzyloxy-4- [N-methyl- (2-cyclo-pentoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-benzyloxy-4- [N-methyl- ( 3-cyclo-pentoxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-benzyloxy-4- [N-methyl- (4-cyclo-pentoxyphenyl) amino] -5- (trifluoromethyl) ) Pyrimidine, 2-benzyloxy-4- [N-methyl- (2-n-hexyloxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-benzyloxy-4- [N-methyl- (3 -N-hexyloxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-benzyloxy-4- [N-methyl- 4-n-hexyloxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-benzyloxy-4- [N-methyl- (2-cyclo-hexyloxyphenyl) amino] -5- (trifluoromethyl) ) Pyrimidine, 2-benzyloxy-4- [N-methyl- (3-cyclo-hexyloxyphenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-benzyloxy-4- [N-methyl- (4 -Cyclo-hexyloxyphenyl) amino] -5- (trifluoromethyl) pyrimidine and the like.
本発明の一般式(2)で表わされる2−ベンジルオキシ−5−(トリフルオロメチル)ピリミジン誘導体でR1がハロゲン原子、シアノ基である化合物としては、具体的には例えば、2−ベンジルオキシ−4−[N−メチル−(2−フルオロフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−ベンジルオキシ−4−[N−メチル−(3−フルオロフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−ベンジルオキシ−4−[N−メチル−(4−フルオロフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−ベンジルオキシ−4−[N−メチル−(2−クロロフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−ベンジルオキシ−4−[N−メチル−(3−クロロフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−ベンジルオキシ−4−[N−メチル−(4−クロロフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−ベンジルオキシ−4−[N−メチル−(2−ブロモフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−ベンジルオキシ−4−[N−メチル−(3−ブロモフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−ベンジルオキシ−4−[N−メチル−(4−ブロモフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−ベンジルオキシ−4−[N−メチル−(2−ヨードフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−ベンジルオキシ−4−[N−メチル−(3−ヨードフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−ベンジルオキシ−4−[N−メチル−(4−ヨードフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−ベンジルオキシ−4−[N−メチル−(2−シアノフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−ベンジルオキシ−4−[N−メチル−(3−シアノフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン、2−ベンジルオキシ−4−[N−メチル−(4−シアノフェニル)アミノ]−5−(トリフルオロメチル)ピリミジン等が挙げられる。 Specific examples of the 2-benzyloxy-5- (trifluoromethyl) pyrimidine derivative represented by the general formula (2) of the present invention in which R 1 is a halogen atom or a cyano group include 2-benzyloxy -4- [N-methyl- (2-fluorophenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-benzyloxy-4- [N-methyl- (3-fluorophenyl) amino] -5- ( Trifluoromethyl) pyrimidine, 2-benzyloxy-4- [N-methyl- (4-fluorophenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-benzyloxy-4- [N-methyl- (2 -Chlorophenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-benzyloxy-4- [N-methyl- (3-chlorophenyl) ami ] -5- (trifluoromethyl) pyrimidine, 2-benzyloxy-4- [N-methyl- (4-chlorophenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-benzyloxy-4- [N- Methyl- (2-bromophenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-benzyloxy-4- [N-methyl- (3-bromophenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-Benzyloxy-4- [N-methyl- (4-bromophenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-benzyloxy-4- [N-methyl- (2-iodophenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-benzyloxy-4- [N-methyl- (3-iodophenyl) amino] -5- (trifluoro) Oromethyl) pyrimidine, 2-benzyloxy-4- [N-methyl- (4-iodophenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-benzyloxy-4- [N-methyl- (2-cyano) Phenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-benzyloxy-4- [N-methyl- (3-cyanophenyl) amino] -5- (trifluoromethyl) pyrimidine, 2-benzyloxy-4 -[N-methyl- (4-cyanophenyl) amino] -5- (trifluoromethyl) pyrimidine and the like.
本発明において、これらの一般式(2)で表わされる2−ベンジルオキシ−5−(トリフルオロメチル)ピリミジン誘導体の内でも、R1が水素原子、メチル基又はエチル基である化合物が好適に用いられる。
本発明の一般式(3)で表わされる金属アルコキド類としては、具体的には例えば、リチウムメトキシド、ナトリウムメトキシド、カリウムメトキシド、リチウムエトキシド、ナトリウムエトキシド、カリウムエトキシド、リチウム−n−プロポキド、ナトリウム−n−プロポキド、カリウム−n−プロポキシド、リチウム−iso−プロポキド、ナトリウム−iso−プロポキド、カリウム−iso−プロポキシド、リチウム−n−ブトキシド、ナトリウム−n−ブトキシド、カリウム−n−ブトキシド、リチウム−iso−ブトキシド、ナトリウム−iso−ブトキシド、カリウム−iso−ブトキシド、リチウム−sec−ブトキシド、ナトリウム−sec−ブトキシド、カリウム−sec−ブトキシド、リチウム−tert−ブトキシド、ナトリウム−tert−ブトキシド、カリウム−tert−ブトキシド、リチウム−n−ペントキシド、ナトリウム−n−ペントキシド、カリウム−n−ペントキシド、リチウム−cyclo−ペントキシド、ナトリウム−cyclo−ペントキシド、カリウム−cyclo−ペントキシド、リチウム−n−ヘキシルオキシド、ナトリウム−n−ヘキシルオキシド、カリウム−n−ヘキシルオキシド、リチウム−cyclo−ヘキシルオキシド、ナトリウム−cyclo−ヘキシルオキシド、カリウム−cyclo−ヘキシルオキシド等が挙げられ、反応に具する一般式(2)で表わされる2−ベンジルオキシ−5−(トリフルオロメチル)ピリミジン誘導体に対して、1.2モル量〜10.0モル量使用するとよい。
In the present invention, among the 2-benzyloxy-5- (trifluoromethyl) pyrimidine derivatives represented by the general formula (2), compounds in which R 1 is a hydrogen atom, a methyl group or an ethyl group are preferably used. It is done.
Specific examples of the metal alkoxides represented by the general formula (3) of the present invention include lithium methoxide, sodium methoxide, potassium methoxide, lithium ethoxide, sodium ethoxide, potassium ethoxide, and lithium-n. -Propoxide, sodium-n-propoxide, potassium-n-propoxide, lithium-iso-propoxide, sodium-iso-propoxide, potassium-iso-propoxide, lithium-n-butoxide, sodium-n-butoxide, potassium-n -Butoxide, lithium-iso-butoxide, sodium-iso-butoxide, potassium-iso-butoxide, lithium-sec-butoxide, sodium-sec-butoxide, potassium-sec-butoxide, lithium-tert-butoxide Sodium-tert-butoxide, potassium-tert-butoxide, lithium-n-pentoxide, sodium-n-pentoxide, potassium-n-pentoxide, lithium-cyclo-pentoxide, sodium-cyclo-pentoxide, potassium-cyclo-pentoxide, Lithium-n-hexyl oxide, sodium-n-hexyl oxide, potassium-n-hexyl oxide, lithium-cyclo-hexyl oxide, sodium-cyclo-hexyl oxide, potassium-cyclo-hexyl oxide, etc. It is good to use 1.2 mol amount-10.0 mol amount with respect to the 2-benzyloxy-5- (trifluoromethyl) pyrimidine derivative represented by General formula (2).
本発明の一般式(1)で表わされる2−アルコキシ−5−(トリフルオロメチル)ピリミジン誘導体の製造に適用可能な溶剤としては、反応に不活性な溶剤であればあらゆるものが使用可能であるが、例えば、ジエチルエーテル、ジイソプロピルエーテル、メチル−tert−ブチルエーテル、メチルシクロペンチルエーテル、テトラヒドロフラン等のエーテル系溶剤、n−ペンタン、n−ヘキサン、cyclo−ヘキサン等の脂肪族炭化水素系溶剤、ベンゼン、トルエン、エチルベンゼン、キシレン、メシチレン、クメン等の芳香族炭化水素系溶剤、ジクロロメタン、クロロホルム、1,2−ジクロロエタン等のハロゲン化炭化水素系溶剤等が挙げられ、反応に具する式(2)で表わされる2−ベンジルオキシ−5−(トリフルオロメチル)ピリミジン誘導体に対して、2重量倍量〜100重量倍量使用するとよい。また、これら溶剤は2種以上を混合して用いても良い。 As the solvent applicable to the production of the 2-alkoxy-5- (trifluoromethyl) pyrimidine derivative represented by the general formula (1) of the present invention, any solvent that is inert to the reaction can be used. For example, ether solvents such as diethyl ether, diisopropyl ether, methyl-tert-butyl ether, methylcyclopentyl ether, tetrahydrofuran, aliphatic hydrocarbon solvents such as n-pentane, n-hexane, cyclo-hexane, benzene, toluene And aromatic hydrocarbon solvents such as ethylbenzene, xylene, mesitylene and cumene, and halogenated hydrocarbon solvents such as dichloromethane, chloroform and 1,2-dichloroethane, and the like. 2-Benzyloxy-5- (trifluoromethyl Respect pyrimidine derivatives, may be used 2 times by weight to 100 times by weight. Moreover, you may use these solvents in mixture of 2 or more types.
本発明の一般式(1)で表わされる2−アルコキシ−5−(トリフルオロメチル)ピリミジン誘導体の製造の反応温度及び時間としては、反応に用いる2−ベンジルオキシ−5−(トリフルオロメチル)ピリミジン誘導体の種類、金属アルコキシドの種類、溶剤の種類及び基質濃度により異なるが、通常20℃〜120℃の温度範囲で、1時間〜150時間反応を行うことにより反応を完結できる。 As the reaction temperature and time for producing the 2-alkoxy-5- (trifluoromethyl) pyrimidine derivative represented by the general formula (1) of the present invention, 2-benzyloxy-5- (trifluoromethyl) pyrimidine used in the reaction is used. Although depending on the type of derivative, the type of metal alkoxide, the type of solvent and the substrate concentration, the reaction can usually be completed by carrying out the reaction for 1 hour to 150 hours in a temperature range of 20 ° C to 120 ° C.
本発明の一般式(1)で表わされる2−アルコキシ−5−(トリフルオロメチル)ピリミジン誘導体の製造後の後処理としては、周知の方応で実施可能で、例えば、飽和塩化アンモニウム水溶液で中和、ジクロロメタン等の溶剤で抽出、硫酸ナトリウム上で乾燥、ろ過、濃縮することにより、粗製物を得、再結晶またはシリカゲルカラムクロマトグラフィー等により精製し目的物の2−アルコキシ−5−(トリフルオロメチル)ピリミジン誘導体を得ることができる。 The post-treatment after the production of the 2-alkoxy-5- (trifluoromethyl) pyrimidine derivative represented by the general formula (1) of the present invention can be carried out in a well-known manner, for example, with a saturated aqueous ammonium chloride solution. A crude product is obtained by extraction with a solvent such as sum, dichloromethane, etc., drying over sodium sulfate, filtration and concentration, and purification by recrystallization or silica gel column chromatography or the like to obtain the desired 2-alkoxy-5- (trifluoro). A methyl) pyrimidine derivative can be obtained.
以下実施例により本発明を具体的に説明するが、本発明はこれらの実施例のみに限定されるものではない。
なお、分析に当たっては下記機器を使用した。
1H−NMR,19F−NMR,13C−NMR:ブルカー(BRUKER)社製AVANCE II 400。
EXAMPLES The present invention will be specifically described below with reference to examples, but the present invention is not limited only to these examples.
The following equipment was used for the analysis.
1 H-NMR, 19 F-NMR, 13 C-NMR: AVANCE II 400 manufactured by Bruker.
GC-MS:嶋津製作所製GCMS−QP2010Plus。
元素分析:ヤナコ社製CHNコーダー MT−6。
参考例1 2−ベンジルオキシ−4−クロロ−5−(トリフルオロメチル)ピリミジン(4)の調製
GC-MS: Shimadzu GCMS-QP2010Plus.
Elemental analysis: CHN coder MT-6 manufactured by Yanaco.
Reference Example 1 Preparation of 2-benzyloxy-4-chloro-5- (trifluoromethyl) pyrimidine (4)
撹拌子を備え、窒素置換した50mLのナス型フラスコに、ベンジルアルコール(0.50g,4.61mmol)及びテトラヒドロフラン(4mL)を仕込み、−20℃に冷却の後、n−ブチルリチウム(1.6M−ヘキサン溶液,2.88mL,4.61mmol)を添加し、同温度で30分撹拌した。次いで、ヘキサン(8mL)を添加した後、−80℃に冷却し、2,4−ジクロロ−5−(トリフルオロメチル)ピリミジン(1.00g,4.61mmol)を添加した。さらに同温度で30分撹拌の後、室温に戻し、2時間反応を行った。 A 50 mL eggplant-shaped flask equipped with a stirring bar and charged with nitrogen was charged with benzyl alcohol (0.50 g, 4.61 mmol) and tetrahydrofuran (4 mL). After cooling to −20 ° C., n-butyllithium (1.6 M -Hexane solution, 2.88 mL, 4.61 mmol) was added, and the mixture was stirred at the same temperature for 30 minutes. Then, hexane (8 mL) was added, then cooled to −80 ° C., and 2,4-dichloro-5- (trifluoromethyl) pyrimidine (1.00 g, 4.61 mmol) was added. Further, the mixture was stirred at the same temperature for 30 minutes, then returned to room temperature and reacted for 2 hours.
反応終了後、飽和塩化アンモニウム水溶液(10mL)を添加、減圧濃縮によりテトラヒロロフランを留去、ジクロロメタン(10mL×3回)抽出、有機層を合わせて、硫酸ナトリウム上で乾燥、ろ過、次いで濃縮することにより、粗製物の2−ベンジルオキシ4−クロロ−5−(トリフルオロメチル)ピリミジンを淡黄色固体として得た(1.41g)。得られた粗製物を、ヘキサフルオロベンゼンを内部標準として用いた19F−NMR測定において、転化率100%、収率90%、副生物の2−クロロ−4−ベンジルオキシ−5−(トリフルロメチル)ピリミジンが収率換算で10%含有されていた。 After completion of the reaction, a saturated aqueous solution of ammonium chloride (10 mL) is added. Tetrachlorofuran is distilled off by concentration under reduced pressure, extraction with dichloromethane (10 mL × 3 times), the organic layers are combined, dried over sodium sulfate, filtered, and concentrated. This gave crude 2-benzyloxy 4-chloro-5- (trifluoromethyl) pyrimidine as a pale yellow solid (1.41 g). The obtained crude product was subjected to 19 F-NMR measurement using hexafluorobenzene as an internal standard. The conversion rate was 100%, the yield was 90%, and the by-product 2-chloro-4-benzyloxy-5- (trifluoro) 10% of methyl) pyrimidine was contained in terms of yield.
さらに得られた粗製物を、エチルベンゼンを用いた再結晶を行うことにより、精製2−ベンジルオキシ−4−クロロ−5−(トリフルオロメチル)ピリミジン(4)を白色固体として得た(1.00g,収率75%、純度99%)。
1H−NMR(CDCl3,400MHz)δ8.70(d,J=0.8Hz,1H),7.50−7.45(m,2H),7.40−7.32(m,3H),5.50(s,2H)。
19F−NMR(CDCl3,376MHz)δ−63.62。
13C−NMR(CDCl3,100MHz)δ165.94,161.08,158.70(q,J=5.0Hz),135.05,128.75,128.57,122.31(q,J=270.0Hz),117.50(q,J=33.8Hz),70.95。
GC−MS(m/z):288(M+,31),253(35),182(27),107(66),91(100)。
元素分析
計算値 炭素(49.93%)、水素(2.79%)、窒素(9.70%)。
測定値 炭素(19.80%)、水素(2.80%)、窒素(9.68%)。
Further, the obtained crude product was recrystallized with ethylbenzene to obtain purified 2-benzyloxy-4-chloro-5- (trifluoromethyl) pyrimidine (4) as a white solid (1.00 g). , Yield 75%, purity 99%).
1 H-NMR (CDCl 3 , 400 MHz) δ 8.70 (d, J = 0.8 Hz, 1H), 7.50-7.45 (m, 2H), 7.40-7.32 (m, 3H) , 5.50 (s, 2H).
19 F-NMR (CDCl 3 , 376 MHz) δ-63.62.
13 C-NMR (CDCl 3 , 100 MHz) δ 165.94, 161.08, 158.70 (q, J = 5.0 Hz), 135.05, 128.75, 128.57, 122.31 (q, J = 270.0 Hz), 117.50 (q, J = 33.8 Hz), 70.95.
GC-MS (m / z): 288 (M + , 31), 253 (35), 182 (27), 107 (66), 91 (100).
Elemental analysis calculated: carbon (49.93%), hydrogen (2.79%), nitrogen (9.70%).
Measurements Carbon (19.80%), hydrogen (2.80%), nitrogen (9.68%).
参考例2 2−ベンジルオキシ−4−(N−メチルフェニルアミノ)−5−(トリフルオロメチル)ピリミジン(5)の調製 Reference Example 2 Preparation of 2-benzyloxy-4- (N-methylphenylamino) -5- (trifluoromethyl) pyrimidine (5)
撹拌子を備え、窒素置換した50mLのナス型フラスコに、参考例1で調製した2−ベンジルオキシ−4−クロロ−5−(トリフルオロメチル)ピリミジン(2)(200mg,0.693mmol)、N−メチルアニリン(89.1mg,0.831mmol)、N,N−ジイソプロピルエチルアミン(116mg,0.900mmol)及びトルエン(4mL)を仕込み、110℃で93時間反応を行った。 To a 50 mL eggplant-shaped flask equipped with a stir bar and purged with nitrogen, 2-benzyloxy-4-chloro-5- (trifluoromethyl) pyrimidine (2) (200 mg, 0.693 mmol) prepared in Reference Example 1, N -Methylaniline (89.1 mg, 0.831 mmol), N, N-diisopropylethylamine (116 mg, 0.900 mmol) and toluene (4 mL) were charged and reacted at 110 ° C. for 93 hours.
反応終了後、室温まで冷却、飽和塩化アンモニウム水溶液(5mL)添加、分液、水層をジクロロメタン抽出(5ml×3回)、有機層を合わせて硫酸ナトリウム上で乾燥、ろ過、濃縮し、粗製物(238mg)を得た。得られた粗製物を、ヘキサフルオロベンゼンを内部標準として用いた19F−NMR測定において、転化率98%、収率68%で、目的物の2−ベンジルオキシ−4−(N−メチルフェニルアミノ)−5−(トリフルオロメチル)ピリミジン(5)(169mg,0.471mmol)が生成していた。 After completion of the reaction, the mixture was cooled to room temperature, saturated aqueous ammonium chloride solution (5 mL) was added, liquid separation, the aqueous layer was extracted with dichloromethane (5 ml × 3 times), and the organic layers were combined, dried over sodium sulfate, filtered, concentrated, and crude. (238 mg) was obtained. The obtained crude product was converted into a target 2-benzyloxy-4- (N-methylphenylamino) in a 19 F-NMR measurement using hexafluorobenzene as an internal standard with a conversion of 98% and a yield of 68%. ) -5- (trifluoromethyl) pyrimidine (5) (169 mg, 0.471 mmol) was produced.
さらに、得られた粗製物を、ヘキサンで再結晶することにより、精製2−ベンジルオキシ−4−(N−メチルフェニルアミノ)−5−(トリフルオロメチル)ピリミジン(5)を黄色固体として得た(122mg,0.340mmol,収率49%)。
1H−NMR(CDCl3,400MHz)δ8.40(s,1H),7.46−7.12(m,10H),5.44(s,2H),3.45(s,3H)。
19F−NMR(CDCl3,376MHz)δ−58.23。
13C−NMR(CDCl3,100MHz)δ165.40,162.13,159.31(q,J=6.1Hz),146.22,136.44,129.39,128.47,128.09,127.52,127.19,127.00,123.48(q,J=269.5Hz),105.34(q,J=32.8Hz),69.30,42.71。
GC−MS(m/z)359(M+,18),358(31),268(11),252(13),220(9),106(22),91(100),77(17),65(16)。
Further, the obtained crude product was recrystallized from hexane to obtain purified 2-benzyloxy-4- (N-methylphenylamino) -5- (trifluoromethyl) pyrimidine (5) as a yellow solid. (122 mg, 0.340 mmol, 49% yield).
1 H-NMR (CDCl 3 , 400 MHz) δ 8.40 (s, 1H), 7.46-7.12 (m, 10H), 5.44 (s, 2H), 3.45 (s, 3H).
19 F-NMR (CDCl 3 , 376 MHz) δ-58.23.
13 C-NMR (CDCl 3 , 100 MHz) δ 165.40, 162.13, 159.31 (q, J = 6.1 Hz), 146.22, 136.44, 129.39, 128.47, 128.09 127.52, 127.19, 127.00, 123.48 (q, J = 269.5 Hz), 105.34 (q, J = 32.8 Hz), 69.30, 42.71.
GC-MS (m / z) 359 (M + , 18), 358 (31), 268 (11), 252 (13), 220 (9), 106 (22), 91 (100), 77 (17) 65 (16).
実施例1 2−メトキシ−4−(N−メチルフェニルアミノ)−5−(トリフルオロメチル)ピリミジン(6)の調製 Example 1 Preparation of 2-methoxy-4- (N-methylphenylamino) -5- (trifluoromethyl) pyrimidine (6)
撹拌子を備えた5mLのナス型フラスコに、参考例2で調製した2−ベンジルオキシ−4−(N−メチルフェニルアミノ)−5−(トリフルオロメチル)ピリミジン(5)(109.0mg,0.304mmol)及びテトラヒドロフラン(1mL)を仕込み、撹拌しながら20℃とした。次いでこれにメタノール(30.7mg,0.958mmol)、ナトリウムヘキサメチルジシラジド(1.0M−THF溶液,0.912mL,0.912mmol)及びテトラヒドロフラン(1mL)より調製したナトリウムメトキシドのテトラヒドロフラン溶液を滴下した後、さらに同温度で4時間反応を行った。 To a 5 mL eggplant-shaped flask equipped with a stir bar, 2-benzyloxy-4- (N-methylphenylamino) -5- (trifluoromethyl) pyrimidine (5) (109.0 mg, 0) prepared in Reference Example 2 was prepared. .304 mmol) and tetrahydrofuran (1 mL) were added, and the mixture was stirred at 20 ° C. Next, a tetrahydrofuran solution of sodium methoxide prepared from methanol (30.7 mg, 0.958 mmol), sodium hexamethyldisilazide (1.0 M-THF solution, 0.912 mL, 0.912 mmol) and tetrahydrofuran (1 mL). Then, the reaction was further carried out at the same temperature for 4 hours.
反応終了後、飽和の塩化アンモニウム水溶液(2mL)を添加、分液、ジクロロメタンで抽出(2mL×3回)、硫酸ナトリウム上で乾燥、ろ過、濃縮ことにより粗製物を得た(98.3mg)。得られた粗製物を、ヘキサフルオロベンゼンを内部標準物質として用いた19F−NMRの測定において、目的物の2−メトキシ−4−(N−メチルフェニルアミノ)−5−(トリフルオロメチル)ピリミジンの(6)(65.4mg,0.231mmol)が生成していた。(収率76%)。 After completion of the reaction, a saturated aqueous ammonium chloride solution (2 mL) was added, liquid separation, extraction with dichloromethane (2 mL × 3 times), drying over sodium sulfate, filtration and concentration gave a crude product (98.3 mg). The obtained crude product was subjected to 19 F-NMR measurement using hexafluorobenzene as an internal standard substance, and the target 2-methoxy-4- (N-methylphenylamino) -5- (trifluoromethyl) pyrimidine was obtained. (6) (65.4 mg, 0.231 mmol) was produced. (Yield 76%).
得られた粗製物を、シリカゲル薄層クロマトグラフィーで精製することにより、目的物の2−メトキシ−4−(N−メチルフェニルアミノ)−5−(トリフルオロメチル)ピリミジンの(6)(60.2mg,0.213mmol)を得た(収率70%)。
1H−NMR(CDCl3,400MHz)δ8.38(s,1H),7.38−7.13(m,5H),4.01(s,3H),3.47(s,3H)。
19F−NMR(CDCl3,376MHz)δ−58.25。
13C−NMR(CDCl3,100MHz)δ165.87,162.17,159.09(q,J=6.1Hz),146.20,129.46,128.54,127.08,123.46(q,J=268.9Hz),105.30(q,J=33.1Hz),55.04,42.75。
GC−MS(m/z)283(35,M+),282(100),267(10),178(13),163(8),106(37),91(7),77(17),51(5)。
The obtained crude product was purified by silica gel thin layer chromatography to obtain (6) (60. 60) of the desired 2-methoxy-4- (N-methylphenylamino) -5- (trifluoromethyl) pyrimidine. 2 mg, 0.213 mmol) was obtained (70% yield).
1 H-NMR (CDCl 3 , 400 MHz) δ 8.38 (s, 1H), 7.38-7.13 (m, 5H), 4.01 (s, 3H), 3.47 (s, 3H).
19 F-NMR (CDCl 3 , 376 MHz) δ-58.25.
13 C-NMR (CDCl 3 , 100 MHz) δ 165.87, 162.17, 159.09 (q, J = 6.1 Hz), 146.20, 129.46, 128.54, 127.08, 123.46 (Q, J = 268.9 Hz), 105.30 (q, J = 33.1 Hz), 55.04, 42.75.
GC-MS (m / z) 283 (35, M + ), 282 (100), 267 (10), 178 (13), 163 (8), 106 (37), 91 (7), 77 (17) , 51 (5).
実施例2 2−メトキシ−4−(N−メチルフェニルアミノ)−5−(トリフルオロメチル)ピリミジンの(6)の調製
実施例1と同じ反応装置を用い、ナトリウムヘキサメチルジシラジド(1.0M−THF溶液、0.912mL,0.912mmol)に替えて、カリウムヘキサメチルジシラジド(1.0M−THF溶液、0.912mL,0.912mmol)を用い、0℃で24時間反応を行った以外は実施例1と同じ操作を行い、粗製物を得た(102.5mg)。得られた粗製物を、ヘキサフルオロベンゼンを内部標準物質として用いた19F−NMRの測定において、目的物の2−メトキシ−4−(N−メチルフェニルアミノ)−5−(トリフルオロメチル)ピリミジンの(6)(62.0mg,0.219mmol)が生成していた。(収率72%)。
Example 2 Preparation of 2-methoxy-4- (N-methylphenylamino) -5- (trifluoromethyl) pyrimidine (6) Using the same reactor as in Example 1, sodium hexamethyldisilazide (1. In place of 0M-THF solution, 0.912 mL, 0.912 mmol), potassium hexamethyldisilazide (1.0 M-THF solution, 0.912 mL, 0.912 mmol) was used, and the reaction was performed at 0 ° C. for 24 hours. The procedure was the same as in Example 1, except that the crude product was obtained (102.5 mg). The obtained crude product was subjected to 19 F-NMR measurement using hexafluorobenzene as an internal standard substance, and the target 2-methoxy-4- (N-methylphenylamino) -5- (trifluoromethyl) pyrimidine was obtained. (6) (62.0 mg, 0.219 mmol) was produced. (Yield 72%).
実施例3 2−メトキシ−4−(N−メチルフェニルアミノ)−5−(トリフルオロメチル)ピリミジン(6)の調製
実施例1と同じ反応装置を用い、ナトリウムヘキサメチルジシラジド(1.0M−THF溶液、0.912mL,0.912mmol)に替えて、リチウムヘキサメチルジシラジド(1.0M−THF溶液、0.912mL,0.912mmol)を用い、70℃で24時間反応を行った以外は実施例1と同じ操作を行い、粗製物を得た(84.8mg)。得られた粗製物を、ヘキサフルオロベンゼンを内部標準物質として用いた19F−NMRの測定において、目的物の2−メトキシ−4−(N−メチルフェニルアミノ)−5−(トリフルオロメチル)ピリミジンの(6)(36.2mg,0.128mmol)が生成していた。(収率42%)。
Example 3 Preparation of 2-methoxy-4- (N-methylphenylamino) -5- (trifluoromethyl) pyrimidine (6) Using the same reactor as in Example 1, sodium hexamethyldisilazide (1.0 M Instead of THF solution, 0.912 mL, 0.912 mmol), lithium hexamethyldisilazide (1.0 M THF solution, 0.912 mL, 0.912 mmol) was used, and the reaction was performed at 70 ° C. for 24 hours. Otherwise the same operation as in Example 1 was carried out to obtain a crude product (84.8 mg). The obtained crude product was subjected to 19 F-NMR measurement using hexafluorobenzene as an internal standard substance, and the target 2-methoxy-4- (N-methylphenylamino) -5- (trifluoromethyl) pyrimidine was obtained. (6) (36.2 mg, 0.128 mmol) was produced. (Yield 42%).
実施例4 2−メトキシ−4−(N−メチルフェニルアミノ)−5−(トリフルオロメチル)ピリミジンの(6)の調製
実施例1と同じ反応装置を用い、テトラヒドロフラン(1mL)に替えて、n−ヘキサン(1mL)を用い、20℃で2時間反応を行った以外、実施例1と同じ反応操作を行い、粗製物を得た(105.3mg)。得られた粗製物を、ヘキサフルオロベンゼンを内部標準物質として用いた19F−NMRの測定において、目的物の2−メトキシ−4−(N−メチルフェニルアミノ)−5−(トリフルオロメチル)ピリミジンの(6)(74.1mg,0.262mmol)が生成していた。(収率86%)。
Example 4 Preparation of (6-) of 2-methoxy-4- (N-methylphenylamino) -5- (trifluoromethyl) pyrimidine Using the same reaction apparatus as in Example 1, instead of tetrahydrofuran (1 mL), n -The same reaction operation as Example 1 was performed except having reacted at 20 degreeC for 2 hours using hexane (1 mL), and obtained the crude product (105.3 mg). The obtained crude product was subjected to 19 F-NMR measurement using hexafluorobenzene as an internal standard substance, and the target 2-methoxy-4- (N-methylphenylamino) -5- (trifluoromethyl) pyrimidine was obtained. (6) (74.1 mg, 0.262 mmol) was produced. (Yield 86%).
実施例5 2−iso−プロポキシ−4−(N−メチルフェニルアミノ)−5−(トリフルオロメチルピリミジン(7)の調製 Example 5 Preparation of 2-iso-propoxy-4- (N-methylphenylamino) -5- (trifluoromethylpyrimidine (7)
撹拌子を備えた5mLのナス型フラスコに、参考例2で調製した2−ベンジルオキシ−4−(N−メチルフェニルアミノ)−5−(トリフルオロメチル)ピリミジン(5)(109.0mg,0.304mmol)及びヘキサン(1mL)を仕込み、撹拌しながら20℃とした。次いでこれにiso−プロパノール(91.3mg,1.520mmol)、ナトリウムヘキサメチルジシラジド(1.0M−THF溶液,1.520mL,1.520mmol)及びテトラヒドロフラン(1mL)より調製したナトリウム−iso−プロポキシドのテトラヒドロフラン溶液を滴下した後、さらに同温度で1時間反応を行った。 To a 5 mL eggplant-shaped flask equipped with a stir bar, 2-benzyloxy-4- (N-methylphenylamino) -5- (trifluoromethyl) pyrimidine (5) (109.0 mg, 0) prepared in Reference Example 2 was prepared. .304 mmol) and hexane (1 mL) were added, and the mixture was stirred at 20 ° C. Next, sodium-iso- prepared from iso-propanol (91.3 mg, 1.520 mmol), sodium hexamethyldisilazide (1.0 M-THF solution, 1.520 mL, 1.520 mmol) and tetrahydrofuran (1 mL). After dropwise addition of propoxide in tetrahydrofuran, the reaction was further carried out at the same temperature for 1 hour.
反応終了後、飽和の塩化アンモニウム水溶液(2mL)を添加、分液、ジクロロメタンで抽出(2mL×3回)、硫酸ナトリウム上で乾燥、ろ過、濃縮ことにより粗製物を得た(103.4mg)。得られた粗製物を、ヘキサフルオロベンゼンを内部標準物質として用いた19F−NMRの測定において、目的物の2−iso−プロポキシ−4−(N−メチルフェニルアミノ)−5−(トリフルオロメチル)ピリミジンの(7)(81.2mg,0.261mmol)が生成していた。(収率86%)。 After completion of the reaction, a saturated aqueous ammonium chloride solution (2 mL) was added, liquid separation, extraction with dichloromethane (2 mL × 3 times), drying over sodium sulfate, filtration and concentration gave a crude product (103.4 mg). The obtained crude product was subjected to 19 F-NMR measurement using hexafluorobenzene as an internal standard substance, and the desired 2-iso-propoxy-4- (N-methylphenylamino) -5- (trifluoromethyl) was obtained. ) Pyrimidine (7) (81.2 mg, 0.261 mmol) was formed. (Yield 86%).
得られた粗製物を、シリカゲル薄層クロマトグラフィーで精製することにより、目的物の2−iso−プロポキシ−4−(N−メチルフェニルアミノ)−5−(トリフルオロメチル)ピリミジンの(7)(74.7mg,0.240mmol)を得た(収率79%)。
1H−NMR(CDCl3,400MHz)δ8.34(s,1H),7.36−7.12(m,5H),5.26(dq,J=6.2,6.1Hz,1H),3.45(s,3H),1.40(d,J=6.4Hz,6H)。
19F−NMR(CDCl3,376MHz)δ−58.16。
13C−NMR(CDCl3,100MHz)δ165.24,162.30,159.26(q,J=6.2Hz),146.45,129.44,128.58,127.08,123.59(q,J=269.0Hz),105.00(q,J=33.0Hz),71.01,42.68,21.97。
GC−MS(m/z)311(M+,29%),310(33),268(100),252(10),220(10),164(20),150(8),106(57),91(12),77(37)。
The obtained crude product was purified by silica gel thin layer chromatography to obtain the desired 2-iso-propoxy-4- (N-methylphenylamino) -5- (trifluoromethyl) pyrimidine (7) ( (74.7 mg, 0.240 mmol) was obtained (yield 79%).
1 H-NMR (CDCl 3 , 400 MHz) δ 8.34 (s, 1H), 7.36-7.12 (m, 5H), 5.26 (dq, J = 6.2, 6.1 Hz, 1H) 3.45 (s, 3H), 1.40 (d, J = 6.4 Hz, 6H).
19 F-NMR (CDCl 3 , 376 MHz) δ-58.16.
13 C-NMR (CDCl 3 , 100 MHz) δ 165.24, 162.30, 159.26 (q, J = 6.2 Hz), 146.45, 129.44, 128.58, 127.08, 123.59 (Q, J = 269.0 Hz), 105.00 (q, J = 33.0 Hz), 71.01, 42.68, 21.97.
GC-MS (m / z) 311 (M + , 29%), 310 (33), 268 (100), 252 (10), 220 (10), 164 (20), 150 (8), 106 (57 ), 91 (12), 77 (37).
実施例6 2−tert−ブトキシ−4−(N−メチルフェニルアミノ)−5−(トリフルオロメチルピリミジン(8)の調製 Example 6 Preparation of 2-tert-butoxy-4- (N-methylphenylamino) -5- (trifluoromethylpyrimidine (8)
撹拌子を備えた5mLのナス型フラスコに、参考例2で調製した2−ベンジルオキシ−4−(N−メチルフェニルアミノ)−5−(トリフルオロメチル)ピリミジン(5)(109.0mg,0.304mmol)及びn−ヘキサン(1mL)を仕込み、撹拌しながら20℃とした。次いでこれにtert−ブタノール(112.7mg,1.520mmol)、ナトリウムヘキサメチルジシラジド(1.0M−THF溶液,1.520mL,1.520mmol)及びテトラヒドロフラン(1mL)より調製したナトリウム−tert−ブトキシドのテトラヒドロフラン溶液を滴下した後、さらに同温度で26時間反応を行った。 To a 5 mL eggplant-shaped flask equipped with a stir bar, 2-benzyloxy-4- (N-methylphenylamino) -5- (trifluoromethyl) pyrimidine (5) (109.0 mg, 0) prepared in Reference Example 2 was prepared. .304 mmol) and n-hexane (1 mL) were added, and the mixture was stirred at 20 ° C. Next, sodium tert-butanol (112.7 mg, 1.520 mmol), sodium hexamethyldisilazide (1.0 M-THF solution, 1.520 mL, 1.520 mmol) and sodium-tert- prepared from tetrahydrofuran (1 mL) were added thereto. After dropwise addition of a solution of butoxide in tetrahydrofuran, the reaction was further carried out at the same temperature for 26 hours.
反応終了後、飽和の塩化アンモニウム水溶液(2mL)を添加、分液、ジクロロメタンで抽出(2mL×3回)、硫酸ナトリウム上で乾燥、ろ過、濃縮ことにより粗製物を得た(115.8mg)。得られた粗製物を、ヘキサフルオロベンゼンを内部標準物質として用いた19F−NMRの測定において、目的物の2−tert−ブトキシ−4−(N−メチルフェニルアミノ)−5−(トリフルオロメチル)ピリミジンの(8)(67.1mg,0.206mmol)が生成していた。(収率68%)。 After completion of the reaction, a saturated aqueous ammonium chloride solution (2 mL) was added, liquid separation, extraction with dichloromethane (2 mL × 3 times), drying over sodium sulfate, filtration and concentration gave a crude product (115.8 mg). The obtained crude product was subjected to 19 F-NMR measurement using hexafluorobenzene as an internal standard substance, and the target product 2-tert-butoxy-4- (N-methylphenylamino) -5- (trifluoromethyl) was obtained. ) Pyrimidine (8) (67.1 mg, 0.206 mmol) was formed. (Yield 68%).
得られた粗製物を、シリカゲル薄層クロマトグラフィーで精製することにより、目的物の2−tert−ブトキシ−4−(N−メチルフェニルアミノ)−5−(トリフルオロメチル)ピリミジンの(8)(59.7mg,0.184mmol)を得た(収率61%)。
1H−NMR(CDCl3,400MHz)δ8.36(s,1H),7.37−7.13(m,5H),3.46(s,3H),1.59(s,9H)。
19F−NMR(CDCl3,376MHz)δ−58.16。
13C−NMR(CDCl3,100MHz)δ165.01,162.11,159.17(q,J=5.9Hz),146.78,129.52,128.60,127.08,123.79(q,J=269.7Hz),104.42(q,J=33.0Hz),81.75,42.87,28.33。
GC−MS(m/z)325(5,M+),310(5),268(100),220(8),177(6),164(18),150(7),106(40),77(24),41(12)。
The obtained crude product was purified by silica gel thin layer chromatography to obtain the desired 2-tert-butoxy-4- (N-methylphenylamino) -5- (trifluoromethyl) pyrimidine (8) ( (59.7 mg, 0.184 mmol) was obtained (61% yield).
1 H-NMR (CDCl 3 , 400 MHz) δ 8.36 (s, 1H), 7.37-7.13 (m, 5H), 3.46 (s, 3H), 1.59 (s, 9H).
19 F-NMR (CDCl 3 , 376 MHz) δ-58.16.
13 C-NMR (CDCl 3 , 100 MHz) δ 165.01, 162.11, 159.17 (q, J = 5.9 Hz), 146.78, 129.52, 128.60, 127.08, 123.79 (Q, J = 269.7 Hz), 104.42 (q, J = 33.0 Hz), 81.75, 42.87, 28.33.
GC-MS (m / z) 325 (5, M + ), 310 (5), 268 (100), 220 (8), 177 (6), 164 (18), 150 (7), 106 (40) 77 (24), 41 (12).
実施例7 2−cyclo−ヘキシルオキシ−4−(N−メチルフェニルアミノ)−5−(トリフルオロメチルピリミジン(9)の調製 Example 7 Preparation of 2-cyclo-hexyloxy-4- (N-methylphenylamino) -5- (trifluoromethylpyrimidine (9)
撹拌子を備えた5mLのナス型フラスコに、参考例2で調製した2−ベンジルオキシ−4−(N−メチルフェニルアミノ)−5−(トリフルオロメチル)ピリミジン(5)(109.0mg,0.304mmol)及びテトラヒドロフラン(1mL)を仕込み、撹拌しながら20℃とした。次いでこれにcyclo−ヘキサノール(121.8mg,1.216mmol)、ナトリウムヘキサメチルジシラジド(1.0M−THF溶液,1.218mL,1.218mmol)及びテトラヒドロフラン(1mL)より調製したナトリウム−cyclo−ヘキシルオキシドのテトラヒドロフラン溶液を滴下した後、さらに同温度で6時間反応を行った。 To a 5 mL eggplant-shaped flask equipped with a stir bar, 2-benzyloxy-4- (N-methylphenylamino) -5- (trifluoromethyl) pyrimidine (5) (109.0 mg, 0) prepared in Reference Example 2 was prepared. .304 mmol) and tetrahydrofuran (1 mL) were added, and the mixture was stirred at 20 ° C. Next, sodium-cyclo- prepared from cyclo-hexanol (121.8 mg, 1.216 mmol), sodium hexamethyldisilazide (1.0 M-THF solution, 1.218 mL, 1.218 mmol) and tetrahydrofuran (1 mL). After dropwise addition of a hexyl oxide solution in tetrahydrofuran, the reaction was further carried out at the same temperature for 6 hours.
反応終了後、飽和の塩化アンモニウム水溶液(2mL)を添加、分液、ジクロロメタンで抽出(2mL×3回)、硫酸ナトリウム上で乾燥、ろ過、濃縮ことにより粗製物を得た(126.4mg)。得られた粗製物を、ヘキサフルオロベンゼンを内部標準物質として用いた19F−NMRの測定において、目的物の2−cyclo−ヘキシルオキシ−4−(N−メチルフェニルアミノ)−5−(トリフルオロメチル)ピリミジンの(9)(76.7mg,0.218mmol)が生成していた。(収率72%)。 After completion of the reaction, a saturated aqueous ammonium chloride solution (2 mL) was added, liquid separation, extraction with dichloromethane (2 mL × 3 times), drying over sodium sulfate, filtration and concentration gave a crude product (126.4 mg). The obtained crude product was subjected to 19 F-NMR measurement using hexafluorobenzene as an internal standard substance, and the target 2-cyclo-hexyloxy-4- (N-methylphenylamino) -5- (trifluoro) was obtained. Methyl) pyrimidine (9) (76.7 mg, 0.218 mmol) was formed. (Yield 72%).
得られた粗製物を、シリカゲル薄層クロマトグラフィーで精製することにより、目的物の2−cyclo−ヘキシルオキシ−4−(N−メチルフェニルアミノ)−5−(トリフルオロメチル)ピリミジンの(9)(69.1mg,0.197mmol)を得た(収率65%)。
1H−NMR(CDCl3,400MHz)δ8.37(s,1H),7.28−7.12(m,5H),4.95(m,1H),3.45(s,3H),2.06−1.25(m,10H)。
19F−NMR(CDCl3,376MHz)δ−58.07。
13C−NMR(CDCl3,100MHz)δ165.24,162.27,159.30(q,J=6.1Hz),146.50,129.41,127.10,127.06,123.64(q,J=269.3Hz),104.83(q,J=32.8Hz),76.17,42.54,31.77,25.57,24.10。
GC−MS(m/z)351(11),268(100),253(6),220(5),164(12),106(35),77(18),55(11),41(13)。
The obtained crude product was purified by silica gel thin layer chromatography to obtain the desired 2-cyclo-hexyloxy-4- (N-methylphenylamino) -5- (trifluoromethyl) pyrimidine (9). (69.1 mg, 0.197 mmol) was obtained (yield 65%).
1 H-NMR (CDCl 3 , 400 MHz) δ 8.37 (s, 1H), 7.28-7.12 (m, 5H), 4.95 (m, 1H), 3.45 (s, 3H), 2.06-1.25 (m, 10H).
19 F-NMR (CDCl 3 , 376 MHz) δ-58.07.
13 C-NMR (CDCl 3 , 100 MHz) δ 165.24, 162.27, 159.30 (q, J = 6.1 Hz), 146.50, 129.41, 127.10, 127.06, 123.64 (Q, J = 269.3 Hz), 104.83 (q, J = 32.8 Hz), 76.17, 42.54, 31.77, 25.57, 24.10.
GC-MS (m / z) 351 (11), 268 (100), 253 (6), 220 (5), 164 (12), 106 (35), 77 (18), 55 (11), 41 ( 13).
本発明の新規な2−アルコキシ−5−(トリフルオロメチル)ピリミジン誘導体は、各種医薬品の合成中間体として利用可能であり、5−(トリフルオロメチル)ピリミジン骨格の導入剤として期待される。 The novel 2-alkoxy-5- (trifluoromethyl) pyrimidine derivative of the present invention can be used as a synthetic intermediate for various pharmaceuticals, and is expected as an introduction agent for a 5- (trifluoromethyl) pyrimidine skeleton.
Claims (4)
で表される2−アルコキシ−5−(トリフルオロメチル)ピリミジン誘導体。 The following general formula (1)
A 2-alkoxy-5- (trifluoromethyl) pyrimidine derivative represented by:
で表わされる2−ベンジルオキシ−5−(トリフルオロメチル)ピリミジン誘導体と、下記一般式(3)
R2O−Metal (3)
(式(3)中、Metalは金属を示し、R2は前記式(1)に同じ)
で表わされる金属アルコキシドを、反応させる、請求項1または請求項2に記載の一般式(1)で表わされる2−アルコキシ−5−(トリフルオロメチル)ピリミジン誘導体の製造方法。 The following general formula (2)
2-benzyloxy-5- (trifluoromethyl) pyrimidine derivative represented by the following general formula (3)
R 2 O-Metal (3)
(In the formula (3), Metal represents a metal, and R 2 is the same as the formula (1)).
The manufacturing method of the 2-alkoxy-5- (trifluoromethyl) pyrimidine derivative represented by General formula (1) of Claim 1 or Claim 2 with which the metal alkoxide represented by this is made to react.
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