ZA200210035B - Process for the preparation of 2-amino-5,8-dimethoxy [1,2,4]triazolo[1,5-C]pyrimidine. - Google Patents
Process for the preparation of 2-amino-5,8-dimethoxy [1,2,4]triazolo[1,5-C]pyrimidine. Download PDFInfo
- Publication number
- ZA200210035B ZA200210035B ZA200210035A ZA200210035A ZA200210035B ZA 200210035 B ZA200210035 B ZA 200210035B ZA 200210035 A ZA200210035 A ZA 200210035A ZA 200210035 A ZA200210035 A ZA 200210035A ZA 200210035 B ZA200210035 B ZA 200210035B
- Authority
- ZA
- South Africa
- Prior art keywords
- methoxy
- amino
- ome
- triazolo
- formula
- Prior art date
Links
- 238000002360 preparation method Methods 0.000 title claims description 11
- 238000000034 method Methods 0.000 title claims description 10
- DBJPBHJHAPAUQU-UHFFFAOYSA-N 5,8-dimethoxy-[1,2,4]triazolo[1,5-c]pyrimidin-2-amine Chemical compound COC1=CN=C(OC)N2N=C(N)N=C12 DBJPBHJHAPAUQU-UHFFFAOYSA-N 0.000 title description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 22
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 16
- 239000002904 solvent Substances 0.000 claims description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 9
- 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 claims description 6
- PEJFLTBQJYNGOC-UHFFFAOYSA-N (5-methoxypyrimidin-4-yl)hydrazine Chemical compound COC1=CN=CN=C1NN PEJFLTBQJYNGOC-UHFFFAOYSA-N 0.000 claims description 5
- ATDGTVJJHBUTRL-UHFFFAOYSA-N cyanogen bromide Chemical compound BrC#N ATDGTVJJHBUTRL-UHFFFAOYSA-N 0.000 claims description 5
- BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 claims description 5
- 150000001875 compounds Chemical class 0.000 claims description 4
- QPJDMGCKMHUXFD-UHFFFAOYSA-N cyanogen chloride Chemical compound ClC#N QPJDMGCKMHUXFD-UHFFFAOYSA-N 0.000 claims description 4
- 229910052708 sodium Inorganic materials 0.000 claims description 4
- 239000011734 sodium Substances 0.000 claims description 4
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 3
- CTMIYYREUVYVEL-UHFFFAOYSA-N 4-chloro-5-methoxypyrimidine Chemical compound COC1=CN=CN=C1Cl CTMIYYREUVYVEL-UHFFFAOYSA-N 0.000 claims description 2
- 238000002955 isolation Methods 0.000 claims description 2
- 150000003509 tertiary alcohols Chemical class 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 description 11
- NBTOZLQBSIZIKS-UHFFFAOYSA-N methoxide Chemical compound [O-]C NBTOZLQBSIZIKS-UHFFFAOYSA-N 0.000 description 8
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 8
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 230000008707 rearrangement Effects 0.000 description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical group CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- CVICEEPAFUYBJG-UHFFFAOYSA-N 5-chloro-2,2-difluoro-1,3-benzodioxole Chemical group C1=C(Cl)C=C2OC(F)(F)OC2=C1 CVICEEPAFUYBJG-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000003085 diluting agent Substances 0.000 description 3
- 238000004817 gas chromatography Methods 0.000 description 3
- 238000007363 ring formation reaction Methods 0.000 description 3
- 239000002002 slurry Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- SSMSXWXZJUCBMA-UHFFFAOYSA-N (2-chloro-5-methoxypyrimidin-4-yl)hydrazine Chemical compound COC1=CN=C(Cl)N=C1NN SSMSXWXZJUCBMA-UHFFFAOYSA-N 0.000 description 2
- ZTHHRSBDBPCCMZ-UHFFFAOYSA-N 2,4-dichloro-5-methoxypyrimidine Chemical compound COC1=CN=C(Cl)N=C1Cl ZTHHRSBDBPCCMZ-UHFFFAOYSA-N 0.000 description 2
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- 150000004703 alkoxides Chemical group 0.000 description 2
- 239000004009 herbicide Substances 0.000 description 2
- 229910000039 hydrogen halide Inorganic materials 0.000 description 2
- 239000012433 hydrogen halide Substances 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 2
- VFBKWRGTRHKITP-UHFFFAOYSA-N (2,5-dimethoxypyrimidin-4-yl)hydrazine Chemical compound COC1=NC=C(OC)C(NN)=N1 VFBKWRGTRHKITP-UHFFFAOYSA-N 0.000 description 1
- MSXVEPNJUHWQHW-UHFFFAOYSA-N 2-methylbutan-2-ol Chemical compound CCC(C)(C)O MSXVEPNJUHWQHW-UHFFFAOYSA-N 0.000 description 1
- CFOZTZJHBPCPLO-UHFFFAOYSA-N 4-chloro-2,5-dimethoxypyrimidine Chemical compound COC1=CN=C(OC)N=C1Cl CFOZTZJHBPCPLO-UHFFFAOYSA-N 0.000 description 1
- SWERHXRSRVRUFG-UHFFFAOYSA-N 4-chloro-5-methoxy-2-methylsulfanylpyrimidine Chemical compound COC1=CN=C(SC)N=C1Cl SWERHXRSRVRUFG-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 150000008331 benzenesulfonamides Chemical class 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- -1 cyanogen halide Chemical class 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- JMANVNJQNLATNU-UHFFFAOYSA-N glycolonitrile Natural products N#CC#N JMANVNJQNLATNU-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 150000003138 primary alcohols Chemical class 0.000 description 1
- QDGHXQFTWKRQTG-UHFFFAOYSA-N pyrimidin-2-ylhydrazine Chemical class NNC1=NC=CC=N1 QDGHXQFTWKRQTG-UHFFFAOYSA-N 0.000 description 1
- 150000003230 pyrimidines Chemical class 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 150000003333 secondary alcohols Chemical class 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
- YWBFPKPWMSWWEA-UHFFFAOYSA-O triazolopyrimidine Chemical group BrC1=CC=CC(C=2N=C3N=CN[N+]3=C(NCC=3C=CN=CC=3)C=2)=C1 YWBFPKPWMSWWEA-UHFFFAOYSA-O 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US21202400P | 2000-06-16 | 2000-06-16 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200210035B true ZA200210035B (en) | 2003-12-11 |
Family
ID=22789247
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200210035A ZA200210035B (en) | 2000-06-16 | 2002-12-11 | Process for the preparation of 2-amino-5,8-dimethoxy [1,2,4]triazolo[1,5-C]pyrimidine. |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US6362335B2 (ja) |
| EP (1) | EP1289994B1 (ja) |
| JP (1) | JP4223280B2 (ja) |
| KR (1) | KR100800982B1 (ja) |
| CN (1) | CN1172934C (ja) |
| AT (1) | ATE261971T1 (ja) |
| AU (2) | AU6849701A (ja) |
| BR (1) | BR0111993A (ja) |
| DE (1) | DE60102375T2 (ja) |
| DK (1) | DK1289994T3 (ja) |
| HU (1) | HU228907B1 (ja) |
| IL (2) | IL153448A0 (ja) |
| TW (1) | TWI271405B (ja) |
| WO (1) | WO2001098305A1 (ja) |
| ZA (1) | ZA200210035B (ja) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE10019291C2 (de) * | 2000-04-19 | 2002-04-04 | Sueddeutsche Kalkstickstoff | 2-Alkoxy-5-methoxypyrimidine bzw. deren tautomere Formen sowie Verfahren zu deren Herstellung |
| US8038779B2 (en) * | 2006-09-07 | 2011-10-18 | General Electric Company | Methods and apparatus for reducing emissions in an integrated gasification combined cycle |
| CN101486684B (zh) * | 2009-02-20 | 2010-11-10 | 常熟华益化工有限公司 | 2,4-二氯-5-甲氧基嘧啶的制备方法 |
| EP2851367B1 (en) | 2010-05-25 | 2016-10-26 | Dow AgroSciences LLC | Process for the preparation of a 2-amino-5,8-alkoxy[1,2,4]triazolo[1,5-c]pyrimidine by reaction of a 5-halo-8-alkoxy[1,2,4]triazolo[1,5-c]pyrimidin-2-amine with an alkali metal alkoxide in an alcoholic solvent |
| RU2635352C2 (ru) * | 2012-09-14 | 2017-11-13 | ДАУ АГРОСАЙЕНСИЗ ЭлЭлСи | СПОСОБ ПОЛУЧЕНИЯ 2-АМИНО-5,8-ДИМЕТОКСИ[1,2,4]ТРИАЗОЛО[1,5-c]ПИРИМИДИНА ИЗ 4-ХЛОР-2,5-ДИМЕТОКСИПИРИМИДИНА |
| CN103232453A (zh) * | 2013-04-18 | 2013-08-07 | 黑龙江大学 | 2-氨基-5,8-二甲氧基[1,2,4]-三唑并[1,5-c]-嘧啶的合成方法 |
| CN103880846B (zh) * | 2014-03-12 | 2016-09-14 | 泸州东方农化有限公司 | 一种三唑并嘧啶巯基型化合物的制备方法 |
| CN104961662B (zh) * | 2015-06-11 | 2017-05-03 | 湖南化工研究院有限公司 | 2‑氟‑6‑三氟甲基苯磺酰氯的制备方法 |
| CN109400538A (zh) * | 2018-12-19 | 2019-03-01 | 江苏中谱检测有限公司 | 五氟磺草胺原药相关杂质bis-CHYMP的制备方法 |
| CN111848625B (zh) * | 2019-04-24 | 2022-07-26 | 江苏恒瑞医药股份有限公司 | 一种杂芳基并[4,3-c]嘧啶-5-胺类化合物的制备方法及中间体 |
| CN112730689B (zh) * | 2020-12-29 | 2023-04-07 | 营口昌成新材料科技有限公司 | 2-氨基-5,8-二甲氧基[1,2,4]三唑并[1,5-c]嘧啶液相色谱分析方法 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4591588A (en) * | 1984-02-24 | 1986-05-27 | Riker Laboratories, Inc. | Triazolo[1,5-c]pyrimidines and bronchodilation use thereof |
| US5667744A (en) * | 1992-12-22 | 1997-09-16 | Focal Point Products, Inc. | Method for fabricating columns |
| US5480991A (en) * | 1993-11-05 | 1996-01-02 | Dowelanco | 2-Alkoxy-4-hydroazinopyrimidine compounds and their use in the preparation of 5-alkoxy-1,2,4-triazolo[4,3-c]pyrimidine-3(2H)-thione compounds |
| US5858924A (en) * | 1996-09-24 | 1999-01-12 | Dow Agrosciences Llc | N-( 1, 2, 4! triazoloazinyl) benzenesulfonamide and pyridinesulfonamide compounds and their use as herbicides |
-
2001
- 2001-06-15 BR BR0111993-1A patent/BR0111993A/pt not_active Application Discontinuation
- 2001-06-15 DK DK01946446T patent/DK1289994T3/da active
- 2001-06-15 TW TW090114602A patent/TWI271405B/zh not_active IP Right Cessation
- 2001-06-15 JP JP2002504261A patent/JP4223280B2/ja not_active Expired - Fee Related
- 2001-06-15 WO PCT/US2001/019348 patent/WO2001098305A1/en active IP Right Grant
- 2001-06-15 HU HU0301399A patent/HU228907B1/hu not_active IP Right Cessation
- 2001-06-15 AU AU6849701A patent/AU6849701A/xx active Pending
- 2001-06-15 KR KR1020027017066A patent/KR100800982B1/ko not_active IP Right Cessation
- 2001-06-15 EP EP01946446A patent/EP1289994B1/en not_active Expired - Lifetime
- 2001-06-15 US US09/882,657 patent/US6362335B2/en not_active Expired - Lifetime
- 2001-06-15 AU AU2001268497A patent/AU2001268497B2/en not_active Ceased
- 2001-06-15 IL IL15344801A patent/IL153448A0/xx active IP Right Grant
- 2001-06-15 DE DE60102375T patent/DE60102375T2/de not_active Expired - Lifetime
- 2001-06-15 AT AT01946446T patent/ATE261971T1/de active
- 2001-06-15 CN CNB018111696A patent/CN1172934C/zh not_active Expired - Lifetime
-
2002
- 2002-12-11 ZA ZA200210035A patent/ZA200210035B/en unknown
- 2002-12-15 IL IL153448A patent/IL153448A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| HUP0301399A2 (hu) | 2003-08-28 |
| HUP0301399A3 (en) | 2009-01-28 |
| AU6849701A (en) | 2002-01-02 |
| IL153448A (en) | 2006-10-31 |
| JP4223280B2 (ja) | 2009-02-12 |
| CN1436190A (zh) | 2003-08-13 |
| CN1172934C (zh) | 2004-10-27 |
| BR0111993A (pt) | 2003-04-01 |
| EP1289994B1 (en) | 2004-03-17 |
| KR20030010715A (ko) | 2003-02-05 |
| US20020013230A1 (en) | 2002-01-31 |
| DE60102375T2 (de) | 2004-07-29 |
| JP2004501156A (ja) | 2004-01-15 |
| IL153448A0 (en) | 2003-07-06 |
| US6362335B2 (en) | 2002-03-26 |
| KR100800982B1 (ko) | 2008-02-05 |
| DK1289994T3 (da) | 2004-06-21 |
| ATE261971T1 (de) | 2004-04-15 |
| AU2001268497B2 (en) | 2005-08-11 |
| TWI271405B (en) | 2007-01-21 |
| HU228907B1 (hu) | 2013-06-28 |
| EP1289994A1 (en) | 2003-03-12 |
| DE60102375D1 (de) | 2004-04-22 |
| WO2001098305A1 (en) | 2001-12-27 |
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