CN104130198A - 2-氨基-4,6-二甲氧基嘧啶及其制备方法 - Google Patents
2-氨基-4,6-二甲氧基嘧啶及其制备方法 Download PDFInfo
- Publication number
- CN104130198A CN104130198A CN201410322709.3A CN201410322709A CN104130198A CN 104130198 A CN104130198 A CN 104130198A CN 201410322709 A CN201410322709 A CN 201410322709A CN 104130198 A CN104130198 A CN 104130198A
- Authority
- CN
- China
- Prior art keywords
- solvent
- dimethoxy
- reaction
- preparation
- solution
- 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
Links
- 238000002360 preparation method Methods 0.000 title claims abstract description 26
- LVFRCHIUUKWBLR-UHFFFAOYSA-N 4,6-dimethoxypyrimidin-2-amine Chemical compound COC1=CC(OC)=NC(N)=N1 LVFRCHIUUKWBLR-UHFFFAOYSA-N 0.000 title claims abstract description 25
- 238000006243 chemical reaction Methods 0.000 claims abstract description 70
- 239000000243 solution Substances 0.000 claims abstract description 56
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims abstract description 55
- 239000002904 solvent Substances 0.000 claims abstract description 40
- 238000000034 method Methods 0.000 claims abstract description 28
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims abstract description 23
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims abstract description 23
- XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 claims abstract description 21
- 238000003756 stirring Methods 0.000 claims abstract description 20
- CUONGYYJJVDODC-UHFFFAOYSA-N malononitrile Chemical compound N#CCC#N CUONGYYJJVDODC-UHFFFAOYSA-N 0.000 claims abstract description 13
- 239000003054 catalyst Substances 0.000 claims abstract description 11
- 239000000725 suspension Substances 0.000 claims abstract description 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 63
- 125000001891 dimethoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 44
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 42
- 150000001409 amidines Chemical class 0.000 claims description 42
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 39
- 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 27
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 26
- 239000011259 mixed solution Substances 0.000 claims description 19
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 18
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 16
- 238000000926 separation method Methods 0.000 claims description 16
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims description 15
- BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 claims description 13
- 229910000397 disodium phosphate Inorganic materials 0.000 claims description 13
- 235000019800 disodium phosphate Nutrition 0.000 claims description 13
- 238000004821 distillation Methods 0.000 claims description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 13
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 12
- 239000012043 crude product Substances 0.000 claims description 12
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 12
- 239000007788 liquid Substances 0.000 claims description 10
- 239000003960 organic solvent Substances 0.000 claims description 10
- 238000011084 recovery Methods 0.000 claims description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 9
- JJNZXLAFIPKXIG-UHFFFAOYSA-N 2-Chlorobenzylidenemalononitrile Chemical compound ClC1=CC=CC=C1C=C(C#N)C#N JJNZXLAFIPKXIG-UHFFFAOYSA-N 0.000 claims description 7
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 claims description 7
- 239000004327 boric acid Substances 0.000 claims description 7
- 238000010792 warming Methods 0.000 claims description 7
- 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 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 6
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims description 6
- 235000019253 formic acid Nutrition 0.000 claims description 6
- 229910000030 sodium bicarbonate Inorganic materials 0.000 claims description 6
- 235000017557 sodium bicarbonate Nutrition 0.000 claims description 6
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 claims description 5
- 239000000203 mixture Substances 0.000 claims description 5
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 3
- 235000011054 acetic acid Nutrition 0.000 claims description 3
- 235000012538 ammonium bicarbonate Nutrition 0.000 claims description 3
- 239000013078 crystal Substances 0.000 claims description 3
- ZPWVASYFFYYZEW-UHFFFAOYSA-L dipotassium hydrogen phosphate Chemical compound [K+].[K+].OP([O-])([O-])=O ZPWVASYFFYYZEW-UHFFFAOYSA-L 0.000 claims description 3
- 229940045641 monobasic sodium phosphate Drugs 0.000 claims description 3
- 238000001556 precipitation Methods 0.000 claims description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 3
- AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 claims description 3
- 238000005406 washing Methods 0.000 claims description 3
- 239000012467 final product Substances 0.000 abstract description 8
- RAABOESOVLLHRU-UHFFFAOYSA-N diazene Chemical compound N=N RAABOESOVLLHRU-UHFFFAOYSA-N 0.000 abstract description 5
- 229910000071 diazene Inorganic materials 0.000 abstract description 5
- 239000007795 chemical reaction product Substances 0.000 abstract description 3
- 238000002156 mixing Methods 0.000 abstract description 2
- 239000007853 buffer solution Substances 0.000 abstract 2
- 239000000047 product Substances 0.000 description 21
- 238000004519 manufacturing process Methods 0.000 description 10
- 230000000052 comparative effect Effects 0.000 description 9
- 238000001914 filtration Methods 0.000 description 9
- 239000002994 raw material Substances 0.000 description 9
- 239000007789 gas Substances 0.000 description 7
- FFYYHFMMWZGEMB-UHFFFAOYSA-N 4,6-dimethoxypyridin-2-amine Chemical compound COC1=CC(N)=NC(OC)=C1 FFYYHFMMWZGEMB-UHFFFAOYSA-N 0.000 description 5
- 230000008569 process Effects 0.000 description 5
- 241000370738 Chlorion Species 0.000 description 4
- 229940100389 Sulfonylurea Drugs 0.000 description 4
- 239000003905 agrochemical Substances 0.000 description 4
- 230000008901 benefit Effects 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 239000006185 dispersion Substances 0.000 description 4
- 239000003814 drug Substances 0.000 description 4
- 235000021050 feed intake Nutrition 0.000 description 4
- 239000004009 herbicide Substances 0.000 description 4
- 229920002401 polyacrylamide Polymers 0.000 description 4
- -1 sodium alkoxide Chemical class 0.000 description 4
- 229910001220 stainless steel Inorganic materials 0.000 description 4
- 239000010935 stainless steel Substances 0.000 description 4
- YROXIXLRRCOBKF-UHFFFAOYSA-N sulfonylurea Chemical class OC(=N)N=S(=O)=O YROXIXLRRCOBKF-UHFFFAOYSA-N 0.000 description 4
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 4
- 239000012267 brine Substances 0.000 description 3
- 230000002363 herbicidal effect Effects 0.000 description 3
- XJNPVSVLAODWET-UHFFFAOYSA-N methanol;propanedinitrile Chemical compound OC.N#CCC#N XJNPVSVLAODWET-UHFFFAOYSA-N 0.000 description 3
- 239000000575 pesticide Substances 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- 238000007363 ring formation reaction Methods 0.000 description 3
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- 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
- LXYJKVCXSYOZCU-UHFFFAOYSA-N N=NC=NN.N=NC=NN.C(CC(=O)O)(=O)O Chemical compound N=NC=NN.N=NC=NN.C(CC(=O)O)(=O)O LXYJKVCXSYOZCU-UHFFFAOYSA-N 0.000 description 2
- 239000005586 Nicosulfuron Substances 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 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
- 150000003230 pyrimidines Chemical class 0.000 description 2
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 2
- 239000002699 waste material Substances 0.000 description 2
- 101150116295 CAT2 gene Proteins 0.000 description 1
- CGDKALWGXBQBHQ-UHFFFAOYSA-N CC=1C(=O)CC(CC1C)(C)C.N#CC#N.N#CC#N Chemical compound CC=1C(=O)CC(CC1C)(C)C.N#CC#N.N#CC#N CGDKALWGXBQBHQ-UHFFFAOYSA-N 0.000 description 1
- 101100326920 Caenorhabditis elegans ctl-1 gene Proteins 0.000 description 1
- 101100494773 Caenorhabditis elegans ctl-2 gene Proteins 0.000 description 1
- IYXGSMUGOJNHAZ-UHFFFAOYSA-N Ethyl malonate Chemical compound CCOC(=O)CC(=O)OCC IYXGSMUGOJNHAZ-UHFFFAOYSA-N 0.000 description 1
- 101100112369 Fasciola hepatica Cat-1 gene Proteins 0.000 description 1
- AFCARXCZXQIEQB-UHFFFAOYSA-N N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CCNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 AFCARXCZXQIEQB-UHFFFAOYSA-N 0.000 description 1
- 150000007945 N-acyl ureas Chemical class 0.000 description 1
- 101100005271 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) cat-1 gene Proteins 0.000 description 1
- 101100126846 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) katG gene Proteins 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 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 1
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 230000009286 beneficial effect Effects 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
- 229940088623 biologically active substance Drugs 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- GVPFVAHMJGGAJG-UHFFFAOYSA-L cobalt dichloride Chemical compound [Cl-].[Cl-].[Co+2] GVPFVAHMJGGAJG-UHFFFAOYSA-L 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000003912 environmental pollution Methods 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 238000009413 insulation Methods 0.000 description 1
- 239000010977 jade Substances 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 239000000463 material Substances 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
- 238000006116 polymerization reaction Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000012970 tertiary amine catalyst Substances 0.000 description 1
- 231100000167 toxic agent Toxicity 0.000 description 1
- 239000003440 toxic substance Substances 0.000 description 1
- 230000009466 transformation 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
三步总产率(%) | 产品ADMP的纯度(%) |
实施例1 | 84.67 | 99.91 |
实施例2 | 82.10 | 99.81 |
对比例1 | 80.14 | 99.64 |
对比例2 | 72.71 | 99.60 |
Claims (10)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201410322709.3A CN104130198B (zh) | 2014-07-08 | 2014-07-08 | 2-氨基-4,6-二甲氧基嘧啶及其制备方法 |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201410322709.3A CN104130198B (zh) | 2014-07-08 | 2014-07-08 | 2-氨基-4,6-二甲氧基嘧啶及其制备方法 |
Publications (2)
Publication Number | Publication Date |
---|---|
CN104130198A true CN104130198A (zh) | 2014-11-05 |
CN104130198B CN104130198B (zh) | 2016-11-02 |
Family
ID=51803094
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN201410322709.3A Active CN104130198B (zh) | 2014-07-08 | 2014-07-08 | 2-氨基-4,6-二甲氧基嘧啶及其制备方法 |
Country Status (1)
Country | Link |
---|---|
CN (1) | CN104130198B (zh) |
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN105130909A (zh) * | 2015-09-09 | 2015-12-09 | 湖北汇达科技发展有限公司 | 一种2-氨基-4,6-二甲氧基嘧啶的制备方法 |
CN106966993A (zh) * | 2017-04-01 | 2017-07-21 | 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新工艺 |
CN110218192A (zh) * | 2019-07-29 | 2019-09-10 | 南京工业大学 | 一种2-氨基-4,6-二甲氧基嘧啶的制备方法 |
CN110818643A (zh) * | 2018-08-13 | 2020-02-21 | 新发药业有限公司 | 一种2-氨基-4,6-二甲氧基嘧啶的制备方法 |
CN110903251A (zh) * | 2019-12-27 | 2020-03-24 | 江苏丰山集团股份有限公司 | 一种2-氨基-4,6-二甲氧基嘧啶的制备方法 |
Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0024200A1 (en) * | 1979-08-14 | 1981-02-25 | E.I. Du Pont De Nemours And Company | N-Cyanoimidates, their preparation and rearrangement to pyrimidines |
US4412957A (en) * | 1982-06-15 | 1983-11-01 | E. I. Du Pont De Nemours & Co. | Process for preparing dialkyl propanediimidate dihydrohalides |
CN1467206A (zh) * | 2002-07-09 | 2004-01-14 | 金坛希望化工有限公司 | 2-氯-4,6-二甲氧基嘧啶的制备方法 |
CN102285925A (zh) * | 2010-06-18 | 2011-12-21 | 北京英力精化技术发展有限公司 | 2-氯-4,6-二丁氧基嘧啶的合成方法 |
CN102491948A (zh) * | 2011-12-12 | 2012-06-13 | 湖北志诚化工科技有限公司 | 2-氨基-4,6-二甲氧基嘧啶的制备方法 |
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 |
-
2014
- 2014-07-08 CN CN201410322709.3A patent/CN104130198B/zh active Active
Patent Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0024200A1 (en) * | 1979-08-14 | 1981-02-25 | E.I. Du Pont De Nemours And Company | N-Cyanoimidates, their preparation and rearrangement to pyrimidines |
US4412957A (en) * | 1982-06-15 | 1983-11-01 | E. I. Du Pont De Nemours & Co. | Process for preparing dialkyl propanediimidate dihydrohalides |
CN1467206A (zh) * | 2002-07-09 | 2004-01-14 | 金坛希望化工有限公司 | 2-氯-4,6-二甲氧基嘧啶的制备方法 |
CN102285925A (zh) * | 2010-06-18 | 2011-12-21 | 北京英力精化技术发展有限公司 | 2-氯-4,6-二丁氧基嘧啶的合成方法 |
CN102491948A (zh) * | 2011-12-12 | 2012-06-13 | 湖北志诚化工科技有限公司 | 2-氨基-4,6-二甲氧基嘧啶的制备方法 |
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 |
Non-Patent Citations (2)
Title |
---|
李元祥,等: "磺酰脲类除草剂中间体2-氨基-4,6-二甲氧基嘧啶的合成研究进展", 《化工中间体》, no. 5, 31 December 2009 (2009-12-31) * |
陈华,等: "2-氯-4,6-二甲氧基嘧啶的合成", 《化学工业与工程技术》, vol. 27, no. 5, 31 October 2006 (2006-10-31), pages 24 - 25 * |
Cited By (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN105130909A (zh) * | 2015-09-09 | 2015-12-09 | 湖北汇达科技发展有限公司 | 一种2-氨基-4,6-二甲氧基嘧啶的制备方法 |
CN105130909B (zh) * | 2015-09-09 | 2017-11-10 | 湖北汇达科技发展有限公司 | 一种2‑氨基‑4,6‑二甲氧基嘧啶的制备方法 |
CN106966993A (zh) * | 2017-04-01 | 2017-07-21 | 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新工艺 |
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 |
CN110818643A (zh) * | 2018-08-13 | 2020-02-21 | 新发药业有限公司 | 一种2-氨基-4,6-二甲氧基嘧啶的制备方法 |
CN110818643B (zh) * | 2018-08-13 | 2021-04-16 | 新发药业有限公司 | 一种2-氨基-4,6-二甲氧基嘧啶的制备方法 |
CN110218192A (zh) * | 2019-07-29 | 2019-09-10 | 南京工业大学 | 一种2-氨基-4,6-二甲氧基嘧啶的制备方法 |
CN110903251A (zh) * | 2019-12-27 | 2020-03-24 | 江苏丰山集团股份有限公司 | 一种2-氨基-4,6-二甲氧基嘧啶的制备方法 |
CN110903251B (zh) * | 2019-12-27 | 2022-06-14 | 江苏丰山集团股份有限公司 | 一种2-氨基-4,6-二甲氧基嘧啶的制备方法 |
Also Published As
Publication number | Publication date |
---|---|
CN104130198B (zh) | 2016-11-02 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CN104130198A (zh) | 2-氨基-4,6-二甲氧基嘧啶及其制备方法 | |
CN109721545B (zh) | 一种嘧菌酯中间体的制备方法 | |
CN102101847A (zh) | N-甲基-n′-(2-氯乙基)哌嗪的制备方法 | |
CN102816122A (zh) | 一种嘧霉胺的制备方法 | |
CN101544633A (zh) | 甲噻酰胺的合成工艺 | |
CN105130909A (zh) | 一种2-氨基-4,6-二甲氧基嘧啶的制备方法 | |
CN102040561A (zh) | 一种苯并三唑紫外线吸收剂的合成方法 | |
CN105037277B (zh) | 一种3,4‑二氢嘧啶酮/硫酮类杂环化合物的合成方法 | |
CN104529934A (zh) | 一种烟碱类杀虫剂噻虫胺的合成方法 | |
CN101817764A (zh) | 链状尿素衍生物、环状尿素衍生物及噁唑烷酮的制备方法 | |
CN103316696B (zh) | 乙酰柠檬酸三正丁酯的制备方法及所用的催化剂 | |
CN100378073C (zh) | 二吲哚基甲烷及其制备方法 | |
CN104163802A (zh) | 2-氨基噻唑-4-甲酸乙酯的制备方法 | |
CN102808007A (zh) | S-苯基-l-半胱氨酸酶法转化制备方法 | |
CN114195723A (zh) | 一种嘧菌酯的制备方法 | |
CN106316870A (zh) | 一种l‑甘氨酸甲酯盐产品的合成方法 | |
CN112480172A (zh) | 硼烷-吡啶络合物在制备药物化合物中的用途 | |
CN107325013A (zh) | 一种合成甘氨酸丙酰左旋肉碱盐酸盐的方法 | |
CN106866547B (zh) | 2-乙氧基-4,6-二氯嘧啶的合成方法 | |
CN107245043B (zh) | 一种从3-甲硫基丙醛制备3-甲硫基丙醇的制备方法 | |
CN102304102A (zh) | 一种1-甲基哌嗪的制备方法 | |
CN103130247A (zh) | 一种用氯化铵、硫酸生产硫酸铵和氯化氢的工艺 | |
JP2019081758A (ja) | アゾキシストロビンの調製方法 | |
CN101293875B (zh) | 一种合成*唑啉-2-酮的方法 | |
CN106748891A (zh) | 一种苯胺与尿素制备二苯基脲的方法 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
C06 | Publication | ||
PB01 | Publication | ||
C10 | Entry into substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
C14 | Grant of patent or utility model | ||
GR01 | Patent grant | ||
PE01 | Entry into force of the registration of the contract for pledge of patent right |
Denomination of invention: Process for producing 2-amino-4, 6-dichloropyrimidine Effective date of registration: 20181109 Granted publication date: 20161102 Pledgee: Zhongguancun Beijing technology financing Company limited by guarantee Pledgor: BEIJING INSIGHT FINECHEM CO.,LTD.|HUBEI HUIDA TECHNOLOGY DEVELOPMENT Co.,Ltd. Registration number: 2018990001051 |
|
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 |
Date of cancellation: 20210310 Granted publication date: 20161102 Pledgee: Zhongguancun Beijing technology financing Company limited by guarantee Pledgor: BEIJING INSIGHT FINECHEM Co.,Ltd.|HUBEI HUIDA TECHNOLOGY DEVELOPMENT Co.,Ltd. Registration number: 2018990001051 |
|
PC01 | Cancellation 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: 2-amino-4,6-dimethoxypyrimidine and its preparation method Effective date of registration: 20220616 Granted publication date: 20161102 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 | ||
PC01 | Cancellation of the registration of the contract for pledge of patent right |
Date of cancellation: 20230807 Granted publication date: 20161102 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 |
|
PC01 | Cancellation 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: 2-Amino-4,6-dimethoxypyrimidine and its preparation method Effective date of registration: 20230825 Granted publication date: 20161102 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 |
|
PE01 | Entry into force of the registration of the contract for pledge of patent right |