UA73735C2 - A method for the preparation of substituted pirimidines (variants) - Google Patents
A method for the preparation of substituted pirimidines (variants) Download PDFInfo
- Publication number
- UA73735C2 UA73735C2 UA2001117794A UA2001117794A UA73735C2 UA 73735 C2 UA73735 C2 UA 73735C2 UA 2001117794 A UA2001117794 A UA 2001117794A UA 2001117794 A UA2001117794 A UA 2001117794A UA 73735 C2 UA73735 C2 UA 73735C2
- Authority
- UA
- Ukraine
- Prior art keywords
- formula
- group
- haloalkyl
- alkyl
- substituted
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 34
- 238000002360 preparation method Methods 0.000 title abstract description 12
- -1 vinylcarbonyl compound Chemical class 0.000 claims abstract description 34
- 125000005843 halogen group Chemical group 0.000 claims abstract description 18
- 150000001875 compounds Chemical class 0.000 claims abstract description 15
- 239000012442 inert solvent Substances 0.000 claims abstract description 13
- 150000001409 amidines Chemical class 0.000 claims abstract description 11
- 150000003230 pyrimidines Chemical class 0.000 claims abstract description 8
- 150000003839 salts Chemical class 0.000 claims abstract description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 26
- 239000000203 mixture Substances 0.000 claims description 26
- 238000006243 chemical reaction Methods 0.000 claims description 24
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 claims description 19
- 125000001188 haloalkyl group Chemical group 0.000 claims description 19
- 125000000217 alkyl group Chemical group 0.000 claims description 18
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 18
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 13
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical class SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 claims description 12
- YCOYDSQEOWWYDT-UHFFFAOYSA-N 3,3-dichloroprop-2-enal Chemical compound ClC(Cl)=CC=O YCOYDSQEOWWYDT-UHFFFAOYSA-N 0.000 claims description 11
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 11
- 125000003545 alkoxy group Chemical group 0.000 claims description 10
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 9
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 9
- UGEJOEBBMPOJMT-UHFFFAOYSA-N 3-(trifluoromethyl)phenol Chemical compound OC1=CC=CC(C(F)(F)F)=C1 UGEJOEBBMPOJMT-UHFFFAOYSA-N 0.000 claims description 7
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical class OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 7
- DHKHKXVYLBGOIT-UHFFFAOYSA-N 1,1-Diethoxyethane Chemical compound CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 6
- 125000001072 heteroaryl group Chemical group 0.000 claims description 6
- HRKQOINLCJTGBK-UHFFFAOYSA-N dihydroxidosulfur Chemical class OSO HRKQOINLCJTGBK-UHFFFAOYSA-N 0.000 claims description 5
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 5
- 150000004649 carbonic acid derivatives Chemical class 0.000 claims description 4
- 150000003512 tertiary amines Chemical class 0.000 claims description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 3
- HEWZVZIVELJPQZ-UHFFFAOYSA-N 2,2-dimethoxypropane Chemical compound COC(C)(C)OC HEWZVZIVELJPQZ-UHFFFAOYSA-N 0.000 claims description 3
- 125000004199 4-trifluoromethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C(F)(F)F 0.000 claims description 3
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 3
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 claims description 3
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 claims description 3
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 3
- 150000001298 alcohols Chemical class 0.000 claims description 3
- 229950005499 carbon tetrachloride Drugs 0.000 claims description 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 claims description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 3
- 239000008096 xylene Substances 0.000 claims description 3
- 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 claims description 2
- 125000000547 substituted alkyl group Chemical group 0.000 claims 4
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 claims 2
- 238000003756 stirring Methods 0.000 claims 2
- ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 2,3-dimethylbutane Chemical group CC(C)C(C)C ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 0.000 claims 1
- 230000007062 hydrolysis Effects 0.000 claims 1
- 238000006460 hydrolysis reaction Methods 0.000 claims 1
- 238000012876 topography Methods 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 39
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 22
- 238000010438 heat treatment Methods 0.000 description 21
- 239000011541 reaction mixture Substances 0.000 description 13
- 238000004587 chromatography analysis Methods 0.000 description 12
- 239000012074 organic phase Substances 0.000 description 11
- 229910000027 potassium carbonate Inorganic materials 0.000 description 11
- 239000002244 precipitate Substances 0.000 description 11
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
- 239000000741 silica gel Substances 0.000 description 10
- 229910002027 silica gel Inorganic materials 0.000 description 10
- 238000002844 melting Methods 0.000 description 9
- 230000008018 melting Effects 0.000 description 9
- 239000003208 petroleum Substances 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- 150000002170 ethers Chemical class 0.000 description 8
- 125000001424 substituent group Chemical group 0.000 description 7
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- QXQVBEYDHRVIHY-UHFFFAOYSA-N 1,1,1,3-tetrachloro-3-ethoxypropane Chemical compound CCOC(Cl)CC(Cl)(Cl)Cl QXQVBEYDHRVIHY-UHFFFAOYSA-N 0.000 description 4
- XFLGYXVBXUAGQV-UHFFFAOYSA-N 4-(trifluoromethyl)benzenecarboximidamide Chemical compound NC(=N)C1=CC=C(C(F)(F)F)C=C1 XFLGYXVBXUAGQV-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 230000002363 herbicidal effect Effects 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- WEJHBEDHLLBJFW-UHFFFAOYSA-N 4-(trifluoromethyl)benzamide Chemical compound NC(=O)C1=CC=C(C(F)(F)F)C=C1 WEJHBEDHLLBJFW-UHFFFAOYSA-N 0.000 description 3
- YFSYHLNFYUZGGF-UHFFFAOYSA-N 4-(trifluoromethyl)benzamide;hydrochloride Chemical compound Cl.NC(=O)C1=CC=C(C(F)(F)F)C=C1 YFSYHLNFYUZGGF-UHFFFAOYSA-N 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 125000003709 fluoroalkyl group Chemical group 0.000 description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 description 3
- AGYXIUAGBLMBGV-UHFFFAOYSA-N 3,5-dimethylpyrazole-1-carboximidamide;nitric acid Chemical compound O[N+]([O-])=O.CC=1C=C(C)N(C(N)=N)N=1 AGYXIUAGBLMBGV-UHFFFAOYSA-N 0.000 description 2
- PLJCPAJZBGUOCZ-UHFFFAOYSA-N 4-[3-(trifluoromethyl)phenoxy]-2-[4-(trifluoromethyl)phenyl]pyrimidine Chemical compound C1=CC(C(F)(F)F)=CC=C1C1=NC=CC(OC=2C=C(C=CC=2)C(F)(F)F)=N1 PLJCPAJZBGUOCZ-UHFFFAOYSA-N 0.000 description 2
- GXDPRSMVOOTBNL-UHFFFAOYSA-N 4-chlorobenzamide;hydrochloride Chemical compound Cl.NC(=O)C1=CC=C(Cl)C=C1 GXDPRSMVOOTBNL-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 2
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical class C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- FYYLZOKGOFWYEB-UHFFFAOYSA-N acetic acid;4-(trifluoromethyl)benzenecarboximidamide Chemical compound CC([O-])=O.NC(=[NH2+])C1=CC=C(C(F)(F)F)C=C1 FYYLZOKGOFWYEB-UHFFFAOYSA-N 0.000 description 2
- BYFGZMCJNACEKR-UHFFFAOYSA-N aluminium(i) oxide Chemical compound [Al]O[Al] BYFGZMCJNACEKR-UHFFFAOYSA-N 0.000 description 2
- PXXJHWLDUBFPOL-UHFFFAOYSA-N benzamidine Chemical class NC(=N)C1=CC=CC=C1 PXXJHWLDUBFPOL-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical class FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
- JRYOZJIRAVZGMV-UHFFFAOYSA-N cyclopropanecarboximidamide;hydron;chloride Chemical compound Cl.NC(=N)C1CC1 JRYOZJIRAVZGMV-UHFFFAOYSA-N 0.000 description 2
- 125000001153 fluoro group Chemical group F* 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- FCVKLVNLBIBCCU-UHFFFAOYSA-N hydron;pyrazine-2-carboximidamide;chloride Chemical compound Cl.NC(=N)C1=CN=CC=N1 FCVKLVNLBIBCCU-UHFFFAOYSA-N 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000000575 pesticide Substances 0.000 description 2
- 125000004526 pyridazin-2-yl group Chemical group N1N(C=CC=C1)* 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 239000007790 solid phase Substances 0.000 description 2
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 description 1
- 125000004509 1,3,4-oxadiazol-2-yl group Chemical group O1C(=NN=C1)* 0.000 description 1
- 125000004521 1,3,4-thiadiazol-2-yl group Chemical group S1C(=NN=C1)* 0.000 description 1
- BEFIHDBEJKQNKJ-UHFFFAOYSA-N 1-methyl-6-[3-(trifluoromethyl)phenoxy]-2-[4-(trifluoromethyl)phenyl]-2h-pyrimidine Chemical compound CN1C(C=2C=CC(=CC=2)C(F)(F)F)N=CC=C1OC1=CC=CC(C(F)(F)F)=C1 BEFIHDBEJKQNKJ-UHFFFAOYSA-N 0.000 description 1
- GFYFUMNNRPZKQU-UHFFFAOYSA-N 2-(3,5-dimethylpyrazol-1-yl)-4-[3-(trifluoromethyl)phenoxy]pyrimidine Chemical compound N1=C(C)C=C(C)N1C1=NC=CC(OC=2C=C(C=CC=2)C(F)(F)F)=N1 GFYFUMNNRPZKQU-UHFFFAOYSA-N 0.000 description 1
- HKODDOZFJXWWJZ-UHFFFAOYSA-N 2-(4-chlorophenyl)-4-[3-(trifluoromethyl)phenoxy]pyrimidine 3,3-dichloroprop-2-enal Chemical compound ClC(=CC=O)Cl.ClC1=CC=C(C=C1)C1=NC=CC(=N1)OC1=CC(=CC=C1)C(F)(F)F HKODDOZFJXWWJZ-UHFFFAOYSA-N 0.000 description 1
- OKSJFXWTABSDSI-UHFFFAOYSA-N 2-(4-fluorophenyl)-4-[2-methyl-5-(trifluoromethyl)pyrazol-3-yl]oxypyrimidine Chemical compound CN1N=C(C(F)(F)F)C=C1OC1=CC=NC(C=2C=CC(F)=CC=2)=N1 OKSJFXWTABSDSI-UHFFFAOYSA-N 0.000 description 1
- VYLOASWLEVJLKI-UHFFFAOYSA-N 2-(difluoromethoxy)-1h-pyridin-4-one Chemical compound OC1=CC=NC(OC(F)F)=C1 VYLOASWLEVJLKI-UHFFFAOYSA-N 0.000 description 1
- ZOQOPXVJANRGJZ-UHFFFAOYSA-N 2-(trifluoromethyl)phenol Chemical compound OC1=CC=CC=C1C(F)(F)F ZOQOPXVJANRGJZ-UHFFFAOYSA-N 0.000 description 1
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- VYVZRNTUOWITEO-UHFFFAOYSA-N 3,3-bis[3-(trifluoromethyl)phenoxy]prop-2-enal Chemical compound FC(F)(F)C1=CC=CC(OC(OC=2C=C(C=CC=2)C(F)(F)F)=CC=O)=C1 VYVZRNTUOWITEO-UHFFFAOYSA-N 0.000 description 1
- LFRJCVSOTLSQLU-UHFFFAOYSA-N 3,3-dichloroprop-2-enal 4-[3-(trifluoromethyl)phenoxy]-2-[4-(trifluoromethyl)phenyl]pyrimidine Chemical compound ClC(=CC=O)Cl.FC(C=1C=C(OC2=NC(=NC=C2)C2=CC=C(C=C2)C(F)(F)F)C=CC1)(F)F LFRJCVSOTLSQLU-UHFFFAOYSA-N 0.000 description 1
- GBMZWWHKLFBHFS-UHFFFAOYSA-N 3,3-dichloroprop-2-enal;2-(4-fluorophenyl)-4-[3-(trifluoromethyl)phenoxy]pyrimidine Chemical compound ClC(Cl)=CC=O.C1=CC(F)=CC=C1C1=NC=CC(OC=2C=C(C=CC=2)C(F)(F)F)=N1 GBMZWWHKLFBHFS-UHFFFAOYSA-N 0.000 description 1
- LFSUOLATOYPNBS-UHFFFAOYSA-N 3-(fluoromethyl)phenol Chemical compound OC1=CC=CC(CF)=C1 LFSUOLATOYPNBS-UHFFFAOYSA-N 0.000 description 1
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 1
- DRNJIKRLQJRKMM-UHFFFAOYSA-N 4-(trifluoromethyl)benzonitrile Chemical compound FC(F)(F)C1=CC=C(C#N)C=C1 DRNJIKRLQJRKMM-UHFFFAOYSA-N 0.000 description 1
- FLCYTNZRHAXIPN-UHFFFAOYSA-N 4-[2-(difluoromethoxy)pyridin-4-yl]oxy-2-pyrazin-2-ylpyrimidine Chemical compound C1=NC(OC(F)F)=CC(OC=2N=C(N=CC=2)C=2N=CC=NC=2)=C1 FLCYTNZRHAXIPN-UHFFFAOYSA-N 0.000 description 1
- DOPVBZDOHFDAHP-UHFFFAOYSA-N 4-fluorobenzamide;hydrochloride Chemical compound Cl.NC(=O)C1=CC=C(F)C=C1 DOPVBZDOHFDAHP-UHFFFAOYSA-N 0.000 description 1
- JQDATBKJKUWNGA-UHFFFAOYSA-N 4-fluorobenzenecarboximidamide;hydrochloride Chemical compound Cl.NC(=N)C1=CC=C(F)C=C1 JQDATBKJKUWNGA-UHFFFAOYSA-N 0.000 description 1
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 1
- KRBLZKALPKHYIC-UHFFFAOYSA-N 5-methyl-4-[3-(trifluoromethyl)phenoxy]-2-[4-(trifluoromethyl)phenyl]pyrimidine Chemical compound CC1=CN=C(C=2C=CC(=CC=2)C(F)(F)F)N=C1OC1=CC=CC(C(F)(F)F)=C1 KRBLZKALPKHYIC-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 229910015900 BF3 Inorganic materials 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical class C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 1
- NLZUHZJNPQGLLO-UHFFFAOYSA-N [amino-[4-(trifluoromethyl)phenyl]methylidene]azanium;2-sulfanylacetate Chemical compound [O-]C(=O)CS.NC(=[NH2+])C1=CC=C(C(F)(F)F)C=C1 NLZUHZJNPQGLLO-UHFFFAOYSA-N 0.000 description 1
- DREXKZUHNNBVGQ-UHFFFAOYSA-N acetic acid;4-fluorobenzenecarboximidamide Chemical compound CC(O)=O.NC(=N)C1=CC=C(F)C=C1 DREXKZUHNNBVGQ-UHFFFAOYSA-N 0.000 description 1
- WFDIJRYMOXRFFG-UHFFFAOYSA-N acetic anhydride Substances CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 1
- 150000004075 acetic anhydrides Chemical class 0.000 description 1
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 150000003851 azoles Chemical class 0.000 description 1
- PXXJHWLDUBFPOL-UHFFFAOYSA-O benzamidine(1+) Chemical class NC(=[NH2+])C1=CC=CC=C1 PXXJHWLDUBFPOL-UHFFFAOYSA-O 0.000 description 1
- 150000003937 benzamidines Chemical class 0.000 description 1
- LZCZIHQBSCVGRD-UHFFFAOYSA-N benzenecarboximidamide;hydron;chloride Chemical compound [Cl-].NC(=[NH2+])C1=CC=CC=C1 LZCZIHQBSCVGRD-UHFFFAOYSA-N 0.000 description 1
- 150000008359 benzonitriles Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000007942 carboxylates Chemical class 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 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
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 150000004891 diazines Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 125000004995 haloalkylthio group Chemical group 0.000 description 1
- 125000001475 halogen functional group Chemical group 0.000 description 1
- 230000002140 halogenating effect Effects 0.000 description 1
- 230000026030 halogenation Effects 0.000 description 1
- 238000005658 halogenation reaction Methods 0.000 description 1
- 125000005311 halosulfanyl group Chemical group 0.000 description 1
- 230000020169 heat generation Effects 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 150000003854 isothiazoles Chemical class 0.000 description 1
- 238000011031 large-scale manufacturing process Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 150000002823 nitrates Chemical class 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000004287 oxazol-2-yl group Chemical group [H]C1=C([H])N=C(*)O1 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 125000004353 pyrazol-1-yl group Chemical group [H]C1=NN(*)C([H])=C1[H] 0.000 description 1
- 125000004497 pyrazol-5-yl group Chemical group N1N=CC=C1* 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 239000013049 sediment Substances 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 150000004867 thiadiazoles Chemical class 0.000 description 1
- 125000000437 thiazol-2-yl group Chemical group [H]C1=C([H])N=C(*)S1 0.000 description 1
- 150000003557 thiazoles Chemical class 0.000 description 1
- 150000003556 thioamides Chemical class 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- 125000005034 trifluormethylthio group Chemical group FC(S*)(F)F 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/32—One oxygen, sulfur or nitrogen atom
- C07D239/34—One oxygen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/32—One oxygen, sulfur or nitrogen atom
- C07D239/38—One sulfur atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US29244299A | 1999-04-15 | 1999-04-15 | |
| US33352899A | 1999-06-15 | 1999-06-15 | |
| PCT/US2000/009522 WO2000063183A1 (en) | 1999-04-15 | 2000-04-10 | Process for the preparation of substituted pyrimidines |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| UA73735C2 true UA73735C2 (en) | 2005-09-15 |
Family
ID=26967332
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| UA2001117794A UA73735C2 (en) | 1999-04-15 | 2000-10-04 | A method for the preparation of substituted pirimidines (variants) |
Country Status (22)
| Country | Link |
|---|---|
| EP (1) | EP1200414B1 (de) |
| JP (1) | JP2002542233A (de) |
| KR (1) | KR100781851B1 (de) |
| CN (1) | CN1161342C (de) |
| AR (1) | AR023506A1 (de) |
| AT (1) | ATE293608T1 (de) |
| AU (1) | AU780907B2 (de) |
| BR (1) | BR0012736A (de) |
| CA (1) | CA2370285A1 (de) |
| CO (1) | CO4970700A1 (de) |
| CZ (1) | CZ20013691A3 (de) |
| DE (1) | DE60019606T2 (de) |
| ES (1) | ES2240093T3 (de) |
| HU (1) | HUP0200830A3 (de) |
| IL (2) | IL145888A0 (de) |
| MX (1) | MXPA01010390A (de) |
| PL (1) | PL351088A1 (de) |
| PT (1) | PT1200414E (de) |
| SK (1) | SK285728B6 (de) |
| UA (1) | UA73735C2 (de) |
| WO (1) | WO2000063183A1 (de) |
| ZA (1) | ZA200108392B (de) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2001090080A1 (en) * | 2000-05-19 | 2001-11-29 | Basf Aktiengesellschaft | Method of combating undesired plant growth on cereals |
| KR20070011612A (ko) * | 2004-05-19 | 2007-01-24 | 바스프 악티엔게젤샤프트 | 2-치환 피리미딘 및 살충제로서 이의 용도 |
| KR100746582B1 (ko) * | 2005-04-19 | 2007-08-06 | 주식회사 에이스 디지텍 | 디스플레이 장치용 광학필터, 이를 포함하는 디스플레이장치, 및 디스플레이 장치용 광학필터의 제조방법 |
| KR100711858B1 (ko) * | 2005-04-25 | 2007-04-30 | 주식회사 미래건설 | 세탁물도어를 포함하는 지능형 도어 시스템 |
| US8198442B2 (en) | 2005-05-06 | 2012-06-12 | E.I. Du Pont De Nemours And Company | Method for preparation of optionally 2-substituted 1,6-dihydro-6-oxo-4-pyrimidinecarboxylic acids |
| JP5069677B2 (ja) | 2005-05-16 | 2012-11-07 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー | 置換ピリミジンの製造方法 |
| WO2007025898A1 (en) | 2005-09-01 | 2007-03-08 | F. Hoffmann-La Roche Ag | Process for synthesis of aryloxy diaminopyrimidines |
| KR20080053954A (ko) * | 2005-11-03 | 2008-06-16 | 아이알엠 엘엘씨 | 단백질 키나제 억제제 |
| CN106496127B (zh) * | 2016-10-21 | 2019-09-27 | 苏州大学 | 一种多取代嘧啶的制备方法 |
| CN106831603B (zh) * | 2017-01-09 | 2019-07-02 | 辽宁大学 | 一种含氟嘧啶化合物的制备方法 |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH660589A5 (de) * | 1983-01-28 | 1987-05-15 | Lonza Ag | Verfahren zur herstellung von 2-substituierten 5-nitroso-4,6-diamino-pyrimidinen. |
| DE3642832A1 (de) * | 1986-12-16 | 1988-06-30 | Hoechst Ag | Verfahren zur herstellung von aminopyrimidinen |
| DE3642830A1 (de) * | 1986-12-16 | 1988-07-07 | Hoechst Ag | Verfahren zur herstellung von pyrimidinen |
| DK160270C (da) * | 1988-12-16 | 1991-08-05 | Cheminova Agro As | Fremgangsmaade til fremstilling af 2,4- eller 2,4,5-substituerede 6-hydroxypyrimidiner |
| CZ290330B6 (cs) * | 1995-01-26 | 2002-07-17 | American Cyanamid Company | 2,6-Disubstituované pyridinové a 2,4-disubstituované pyrimidinové deriváty, způsob a meziprodukty pro jejich výrobu, jejich pouľití a herbicidní prostředky na jejich bázi a způsob potlačování růstu neľádoucích rostlin |
| SI0802193T1 (en) * | 1996-04-09 | 2002-02-28 | Lonza Ag | Process for the preparation of substituted pyrimidines |
| EP0964855B1 (de) * | 1997-01-13 | 2001-10-17 | Lonza AG | Verfahren zur herstellung von substituierten pyrimidinderivaten |
| AU725548B2 (en) * | 1997-03-11 | 2000-10-12 | E.I. Du Pont De Nemours And Company | Heteroaryl azole herbicides |
| WO1998056789A1 (en) * | 1997-06-10 | 1998-12-17 | E.I. Du Pont De Nemours And Company | Pyrimidinyl azole herbicides |
-
2000
- 2000-04-10 CZ CZ20013691A patent/CZ20013691A3/cs unknown
- 2000-04-10 AU AU43371/00A patent/AU780907B2/en not_active Ceased
- 2000-04-10 KR KR1020017013141A patent/KR100781851B1/ko not_active IP Right Cessation
- 2000-04-10 PL PL00351088A patent/PL351088A1/xx not_active Application Discontinuation
- 2000-04-10 HU HU0200830A patent/HUP0200830A3/hu not_active Application Discontinuation
- 2000-04-10 ES ES00923205T patent/ES2240093T3/es not_active Expired - Lifetime
- 2000-04-10 CA CA002370285A patent/CA2370285A1/en not_active Abandoned
- 2000-04-10 PT PT00923205T patent/PT1200414E/pt unknown
- 2000-04-10 IL IL14588800A patent/IL145888A0/xx active IP Right Grant
- 2000-04-10 MX MXPA01010390A patent/MXPA01010390A/es active IP Right Grant
- 2000-04-10 SK SK1475-2001A patent/SK285728B6/sk not_active IP Right Cessation
- 2000-04-10 EP EP00923205A patent/EP1200414B1/de not_active Expired - Lifetime
- 2000-04-10 WO PCT/US2000/009522 patent/WO2000063183A1/en active Search and Examination
- 2000-04-10 DE DE60019606T patent/DE60019606T2/de not_active Expired - Fee Related
- 2000-04-10 JP JP2000612275A patent/JP2002542233A/ja not_active Withdrawn
- 2000-04-10 BR BR0012736-1A patent/BR0012736A/pt not_active Application Discontinuation
- 2000-04-10 AT AT00923205T patent/ATE293608T1/de not_active IP Right Cessation
- 2000-04-10 CN CNB008079315A patent/CN1161342C/zh not_active Expired - Fee Related
- 2000-04-13 CO CO00027328A patent/CO4970700A1/es unknown
- 2000-04-14 AR ARP000101750A patent/AR023506A1/es unknown
- 2000-10-04 UA UA2001117794A patent/UA73735C2/uk unknown
-
2001
- 2001-10-11 IL IL145888A patent/IL145888A/en unknown
- 2001-10-12 ZA ZA200108392A patent/ZA200108392B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| PT1200414E (pt) | 2005-09-30 |
| AU780907B2 (en) | 2005-04-21 |
| CA2370285A1 (en) | 2000-10-26 |
| ATE293608T1 (de) | 2005-05-15 |
| MXPA01010390A (es) | 2002-03-27 |
| PL351088A1 (en) | 2003-03-24 |
| AU4337100A (en) | 2000-11-02 |
| KR100781851B1 (ko) | 2007-12-03 |
| DE60019606T2 (de) | 2005-08-18 |
| DE60019606D1 (de) | 2005-05-25 |
| HUP0200830A2 (hu) | 2002-07-29 |
| EP1200414B1 (de) | 2005-04-20 |
| ZA200108392B (en) | 2002-12-24 |
| EP1200414A1 (de) | 2002-05-02 |
| IL145888A0 (en) | 2002-07-25 |
| HUP0200830A3 (en) | 2003-04-28 |
| CZ20013691A3 (cs) | 2002-04-17 |
| ES2240093T3 (es) | 2005-10-16 |
| SK14752001A3 (sk) | 2002-05-09 |
| JP2002542233A (ja) | 2002-12-10 |
| KR20020000167A (ko) | 2002-01-04 |
| CN1355792A (zh) | 2002-06-26 |
| WO2000063183A1 (en) | 2000-10-26 |
| IL145888A (en) | 2006-08-20 |
| AR023506A1 (es) | 2002-09-04 |
| CO4970700A1 (es) | 2000-11-07 |
| BR0012736A (pt) | 2005-07-05 |
| CN1161342C (zh) | 2004-08-11 |
| SK285728B6 (sk) | 2007-07-06 |
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