CN105130909B - 一种2‑氨基‑4,6‑二甲氧基嘧啶的制备方法 - Google Patents
一种2‑氨基‑4,6‑二甲氧基嘧啶的制备方法 Download PDFInfo
- Publication number
- CN105130909B CN105130909B CN201510575548.3A CN201510575548A CN105130909B CN 105130909 B CN105130909 B CN 105130909B CN 201510575548 A CN201510575548 A CN 201510575548A CN 105130909 B CN105130909 B CN 105130909B
- Authority
- CN
- China
- Prior art keywords
- amino
- dimethoxy
- preparation
- malononitrile
- catalyst
- 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.)
- Active
Links
- 238000002360 preparation method Methods 0.000 title claims abstract description 18
- GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 title claims abstract description 10
- QHUHPERZCBUMRK-UHFFFAOYSA-N 2,3-dimethoxypyridine Chemical compound COC1=CC=CN=C1OC QHUHPERZCBUMRK-UHFFFAOYSA-N 0.000 title abstract description 3
- CUONGYYJJVDODC-UHFFFAOYSA-N malononitrile Chemical compound N#CCC#N CUONGYYJJVDODC-UHFFFAOYSA-N 0.000 claims abstract description 16
- 238000006243 chemical reaction Methods 0.000 claims abstract description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 31
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 18
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 18
- 239000000243 solution Substances 0.000 claims description 16
- LVFRCHIUUKWBLR-UHFFFAOYSA-N 4,6-dimethoxypyrimidin-2-amine Chemical class COC1=CC(OC)=NC(N)=N1 LVFRCHIUUKWBLR-UHFFFAOYSA-N 0.000 claims description 13
- 150000001409 amidines Chemical class 0.000 claims description 13
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 11
- 239000003054 catalyst Substances 0.000 claims description 11
- 238000003756 stirring Methods 0.000 claims description 11
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims description 10
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims description 10
- 239000002904 solvent Substances 0.000 claims description 10
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims description 9
- OJURWUUOVGOHJZ-UHFFFAOYSA-N methyl 2-[(2-acetyloxyphenyl)methyl-[2-[(2-acetyloxyphenyl)methyl-(2-methoxy-2-oxoethyl)amino]ethyl]amino]acetate Chemical compound C=1C=CC=C(OC(C)=O)C=1CN(CC(=O)OC)CCN(CC(=O)OC)CC1=CC=CC=C1OC(C)=O OJURWUUOVGOHJZ-UHFFFAOYSA-N 0.000 claims description 9
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 8
- 239000007788 liquid Substances 0.000 claims description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 6
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 6
- 125000001891 dimethoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 6
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 claims description 5
- 239000004327 boric acid Substances 0.000 claims description 5
- BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 claims description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 5
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 4
- ATRRKUHOCOJYRX-UHFFFAOYSA-N Ammonium bicarbonate Chemical compound [NH4+].OC([O-])=O ATRRKUHOCOJYRX-UHFFFAOYSA-N 0.000 claims description 4
- XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 claims description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 4
- 239000001099 ammonium carbonate Substances 0.000 claims description 4
- 239000008346 aqueous phase Substances 0.000 claims description 4
- 239000007853 buffer solution Substances 0.000 claims description 4
- 239000013078 crystal Substances 0.000 claims description 4
- 235000019253 formic acid Nutrition 0.000 claims description 4
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical class CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 claims description 3
- 229910000030 sodium bicarbonate Inorganic materials 0.000 claims description 3
- 235000017557 sodium bicarbonate Nutrition 0.000 claims description 3
- 229910000013 Ammonium bicarbonate Inorganic materials 0.000 claims description 2
- 235000011054 acetic acid Nutrition 0.000 claims description 2
- 235000012538 ammonium bicarbonate Nutrition 0.000 claims description 2
- 235000012501 ammonium carbonate Nutrition 0.000 claims description 2
- 235000010338 boric acid Nutrition 0.000 claims description 2
- ZPWVASYFFYYZEW-UHFFFAOYSA-L dipotassium hydrogen phosphate Chemical compound [K+].[K+].OP([O-])([O-])=O ZPWVASYFFYYZEW-UHFFFAOYSA-L 0.000 claims description 2
- 229910000403 monosodium phosphate Inorganic materials 0.000 claims description 2
- 235000019799 monosodium phosphate Nutrition 0.000 claims description 2
- 239000012074 organic phase Substances 0.000 claims description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 2
- AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 claims description 2
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims 1
- MHABMANUFPZXEB-UHFFFAOYSA-N O-demethyl-aloesaponarin I Natural products O=C1C2=CC=CC(O)=C2C(=O)C2=C1C=C(O)C(C(O)=O)=C2C MHABMANUFPZXEB-UHFFFAOYSA-N 0.000 claims 1
- 239000000872 buffer Substances 0.000 claims 1
- 229940113088 dimethylacetamide Drugs 0.000 claims 1
- 150000002118 epoxides Chemical class 0.000 claims 1
- 238000000034 method Methods 0.000 abstract description 22
- 238000007363 ring formation reaction Methods 0.000 abstract description 13
- 238000004519 manufacturing process Methods 0.000 abstract description 9
- 238000005899 aromatization reaction Methods 0.000 abstract description 8
- 230000008901 benefit Effects 0.000 abstract description 4
- 239000002699 waste material Substances 0.000 abstract description 4
- 239000003905 agrochemical Substances 0.000 abstract description 3
- 238000006467 substitution reaction Methods 0.000 abstract description 3
- 230000015572 biosynthetic process Effects 0.000 abstract description 2
- ZIPLUEXSCPLCEI-UHFFFAOYSA-N cyanamide group Chemical group C(#N)[NH-] ZIPLUEXSCPLCEI-UHFFFAOYSA-N 0.000 abstract description 2
- 239000003814 drug Substances 0.000 abstract description 2
- 238000003786 synthesis reaction Methods 0.000 abstract description 2
- 230000008569 process Effects 0.000 description 8
- 239000002994 raw material Substances 0.000 description 7
- RAABOESOVLLHRU-UHFFFAOYSA-N diazene Chemical compound N=N RAABOESOVLLHRU-UHFFFAOYSA-N 0.000 description 6
- 229910000071 diazene Inorganic materials 0.000 description 6
- 238000001914 filtration Methods 0.000 description 4
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- GHUUQSHFGUFUBI-UHFFFAOYSA-N O=C1NC(C1C#N)=O Chemical compound O=C1NC(C1C#N)=O GHUUQSHFGUFUBI-UHFFFAOYSA-N 0.000 description 3
- 239000002270 dispersing agent Substances 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 101150116295 CAT2 gene Proteins 0.000 description 2
- 101100326920 Caenorhabditis elegans ctl-1 gene Proteins 0.000 description 2
- 101100494773 Caenorhabditis elegans ctl-2 gene Proteins 0.000 description 2
- 241000370738 Chlorion Species 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 101100112369 Fasciola hepatica Cat-1 gene Proteins 0.000 description 2
- 239000005514 Flazasulfuron Substances 0.000 description 2
- HWATZEJQIXKWQS-UHFFFAOYSA-N Flazasulfuron Chemical compound COC1=CC(OC)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CN=2)C(F)(F)F)=N1 HWATZEJQIXKWQS-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- 101100005271 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) cat-1 gene Proteins 0.000 description 2
- 101100126846 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) katG gene Proteins 0.000 description 2
- 239000005586 Nicosulfuron Substances 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- VXMNDQDDWDDKOQ-UHFFFAOYSA-N Pyrazosulfuron Chemical compound COC1=CC(OC)=NC(NC(=O)NS(=O)(=O)C=2N(N=CC=2C(O)=O)C)=N1 VXMNDQDDWDDKOQ-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000012267 brine Substances 0.000 description 2
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000002485 combustion reaction Methods 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 239000000428 dust Substances 0.000 description 2
- 230000007613 environmental effect Effects 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 235000021050 feed intake Nutrition 0.000 description 2
- 230000000977 initiatory effect Effects 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- RTCOGUMHFFWOJV-UHFFFAOYSA-N nicosulfuron Chemical compound COC1=CC(OC)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CN=2)C(=O)N(C)C)=N1 RTCOGUMHFFWOJV-UHFFFAOYSA-N 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- 238000005070 sampling Methods 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 235000015424 sodium Nutrition 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 2
- 230000002269 spontaneous effect Effects 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
- 229910001220 stainless steel Inorganic materials 0.000 description 2
- 239000010935 stainless steel Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000010792 warming Methods 0.000 description 2
- 239000005472 Bensulfuron methyl Substances 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-L Malonate Chemical compound [O-]C(=O)CC([O-])=O OFOBLEOULBTSOW-UHFFFAOYSA-L 0.000 description 1
- -1 N, N- dimethylacetamides Amine Chemical class 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
- 229940100389 Sulfonylurea Drugs 0.000 description 1
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- PPWBRCCBKOWDNB-UHFFFAOYSA-N bensulfuron Chemical compound COC1=CC(OC)=NC(NC(=O)NS(=O)(=O)CC=2C(=CC=CC=2)C(O)=O)=N1 PPWBRCCBKOWDNB-UHFFFAOYSA-N 0.000 description 1
- XMQFTWRPUQYINF-UHFFFAOYSA-N bensulfuron-methyl Chemical group COC(=O)C1=CC=CC=C1CS(=O)(=O)NC(=O)NC1=NC(OC)=CC(OC)=N1 XMQFTWRPUQYINF-UHFFFAOYSA-N 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000012295 chemical reaction liquid Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000006837 decompression Effects 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 150000005171 halobenzenes Chemical class 0.000 description 1
- 230000002363 herbicidal effect Effects 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 238000009413 insulation Methods 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 150000003230 pyrimidines Chemical class 0.000 description 1
- 239000012217 radiopharmaceutical Substances 0.000 description 1
- 229940121896 radiopharmaceutical Drugs 0.000 description 1
- 230000002799 radiopharmaceutical effect Effects 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 238000010025 steaming Methods 0.000 description 1
- YROXIXLRRCOBKF-UHFFFAOYSA-N sulfonylurea Chemical class OC(=N)N=S(=O)=O YROXIXLRRCOBKF-UHFFFAOYSA-N 0.000 description 1
- 230000001960 triggered effect Effects 0.000 description 1
- 239000002351 wastewater Substances 0.000 description 1
Classifications
-
- 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
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/52—Two oxygen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Description
Claims (4)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201510575548.3A CN105130909B (zh) | 2015-09-09 | 2015-09-09 | 一种2‑氨基‑4,6‑二甲氧基嘧啶的制备方法 |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201510575548.3A CN105130909B (zh) | 2015-09-09 | 2015-09-09 | 一种2‑氨基‑4,6‑二甲氧基嘧啶的制备方法 |
Publications (2)
Publication Number | Publication Date |
---|---|
CN105130909A CN105130909A (zh) | 2015-12-09 |
CN105130909B true CN105130909B (zh) | 2017-11-10 |
Family
ID=54716542
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN201510575548.3A Active CN105130909B (zh) | 2015-09-09 | 2015-09-09 | 一种2‑氨基‑4,6‑二甲氧基嘧啶的制备方法 |
Country Status (1)
Country | Link |
---|---|
CN (1) | CN105130909B (zh) |
Families Citing this family (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN105601574B (zh) * | 2016-03-17 | 2018-05-11 | 湖北瑞锶科技有限公司 | 一种制备2-氨基-4,6-二甲氧基嘧啶的方法 |
CN106966993B (zh) * | 2017-04-01 | 2019-08-30 | 湖北汇达科技发展有限公司 | 一种2-氨基-4,6-二甲氧基嘧啶制备的粗品后处理工艺 |
CN109293582B (zh) * | 2018-10-29 | 2020-07-31 | 江苏天和制药有限公司 | 一种合成4-氨基-2,6-二甲氧基嘧啶的制备方法 |
CN114230525B (zh) * | 2022-02-24 | 2022-05-13 | 潍坊滨海石油化工有限公司 | 一种2-氨基-4,6-二甲氧基嘧啶的制备方法 |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4288383A (en) * | 1979-08-14 | 1981-09-08 | E. I. Du Pont De Nemours And Company | Propenimidates, their preparation and rearrangement to pyrimidines |
CN103159684A (zh) * | 2011-12-14 | 2013-06-19 | 北京英力精化技术发展有限公司 | 一种2-氨基-4,6-二甲氧基嘧啶的制备方法 |
CN104130198A (zh) * | 2014-07-08 | 2014-11-05 | 北京英力精化技术发展有限公司 | 2-氨基-4,6-二甲氧基嘧啶及其制备方法 |
-
2015
- 2015-09-09 CN CN201510575548.3A patent/CN105130909B/zh active Active
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4288383A (en) * | 1979-08-14 | 1981-09-08 | E. I. Du Pont De Nemours And Company | Propenimidates, their preparation and rearrangement to pyrimidines |
CN103159684A (zh) * | 2011-12-14 | 2013-06-19 | 北京英力精化技术发展有限公司 | 一种2-氨基-4,6-二甲氧基嘧啶的制备方法 |
CN104130198A (zh) * | 2014-07-08 | 2014-11-05 | 北京英力精化技术发展有限公司 | 2-氨基-4,6-二甲氧基嘧啶及其制备方法 |
Non-Patent Citations (1)
Title |
---|
2-氨基-4,6-二甲氧基嘧啶的合成研究;石桂珍 等;《淮阴工学院学报》;20071031;第16卷(第5期);第70-72页 * |
Also Published As
Publication number | Publication date |
---|---|
CN105130909A (zh) | 2015-12-09 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CN105130909B (zh) | 一种2‑氨基‑4,6‑二甲氧基嘧啶的制备方法 | |
CN104725327B (zh) | 一种盐酸厄洛替尼的环保制备方法 | |
CN101219997B (zh) | 一种2-氯-5-氨基嘧啶的合成方法 | |
CN104945299B (zh) | 一种维格列汀的高效合成方法 | |
CN103333120A (zh) | 甲基二磺隆的合成方法 | |
CN106046004A (zh) | 一种1,3,7,9‑四甲基尿酸的全合成方法 | |
CN102079725A (zh) | 一种制备2-氯嘧啶的方法 | |
CN102627594A (zh) | 无水氮丙啶类化合物的制备方法 | |
CN105646373B (zh) | 一种4-氨基-2,6-二甲氧基嘧啶的制备方法 | |
CN103483324B (zh) | 拉帕替尼的新制备方法 | |
CN104130198B (zh) | 2-氨基-4,6-二甲氧基嘧啶及其制备方法 | |
CN109721548B (zh) | 一种嘧菌酯的制备方法 | |
CN107935997A (zh) | 一种奥斯替尼的合成方法 | |
CN102250016B (zh) | 一种4,5,6-三氯嘧啶的制备方法 | |
CN103896941A (zh) | 6-氯咪唑并[1,2-a]吡啶-3-甲腈的合成方法 | |
CN104402813B (zh) | 一种索拉非尼的制备方法 | |
EP2702045B1 (en) | Novel process for the preparation of etravirine | |
CN101798288B (zh) | 嘧啶类化合物的提纯方法 | |
CN102329317B (zh) | 一种可可碱的合成方法 | |
CN101328174B (zh) | 制备3-(2-氯乙基)-2-甲基-4H-吡啶并[1,2-a]嘧啶-4-酮的方法 | |
CN109535074A (zh) | 2-氰基-5-溴吡啶的制备方法 | |
CN110041233A (zh) | N-脂肪酰基-n-甲基牛磺酸钠的制备方法 | |
CN103980190B (zh) | 一种制备2,6-双-(苦氨基)吡啶的方法 | |
CN103539702A (zh) | N’-芳基-n,n-二甲基甲脒的制备新方法 | |
CN106966926B (zh) | 一种lcz696中间体的制备方法 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
C06 | Publication | ||
PB01 | Publication | ||
C10 | Entry into substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
GR01 | Patent grant | ||
GR01 | Patent grant | ||
PE01 | Entry into force of the registration of the contract for pledge of patent right |
Denomination of invention: A preparation method of 2-amino-4,6-dimethoxypyrimidine Effective date of registration: 20220616 Granted publication date: 20171110 Pledgee: Bank of Hubei Co.,Ltd. Jingzhou Development Zone sub branch Pledgor: HUBEI HUIDA TECHNOLOGY DEVELOPMENT Co.,Ltd. Registration number: Y2022980007980 |
|
PE01 | Entry into force of the registration of the contract for pledge of patent right | ||
PC01 | Cancellation of the registration of the contract for pledge of patent right | ||
PC01 | Cancellation of the registration of the contract for pledge of patent right |
Date of cancellation: 20230807 Granted publication date: 20171110 Pledgee: Bank of Hubei Co.,Ltd. Jingzhou Development Zone sub branch Pledgor: BEIJING INSIGHT FINECHEM CO.,LTD.|HUBEI HUIDA TECHNOLOGY DEVELOPMENT Co.,Ltd. Registration number: Y2022980007980 |
|
PE01 | Entry into force of the registration of the contract for pledge of patent right | ||
PE01 | Entry into force of the registration of the contract for pledge of patent right |
Denomination of invention: A preparation method of 2-amino-4,6-dimethoxypyrimidine Effective date of registration: 20230825 Granted publication date: 20171110 Pledgee: Bank of Hubei Co.,Ltd. Jingzhou Development Zone sub branch Pledgor: HUBEI HUIDA TECHNOLOGY DEVELOPMENT Co.,Ltd.|BEIJING INSIGHT FINECHEM CO.,LTD. Registration number: Y2023980053588 |
|
PC01 | Cancellation of the registration of the contract for pledge of patent right |
Granted publication date: 20171110 Pledgee: Bank of Hubei Co.,Ltd. Jingzhou Development Zone sub branch Pledgor: HUBEI HUIDA TECHNOLOGY DEVELOPMENT Co.,Ltd.|BEIJING INSIGHT FINECHEM CO.,LTD. Registration number: Y2023980053588 |