CA2208900A1 - Process for preparing 2-pyrimidinecarboxylates - Google Patents
Process for preparing 2-pyrimidinecarboxylatesInfo
- Publication number
- CA2208900A1 CA2208900A1 CA002208900A CA2208900A CA2208900A1 CA 2208900 A1 CA2208900 A1 CA 2208900A1 CA 002208900 A CA002208900 A CA 002208900A CA 2208900 A CA2208900 A CA 2208900A CA 2208900 A1 CA2208900 A1 CA 2208900A1
- Authority
- CA
- Canada
- Prior art keywords
- alkyl
- preparing
- alkoxy
- pyrimidinecarboxylates
- halopyrimidine
- 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
- ZFCHNZDUMIOWFV-UHFFFAOYSA-N pyrimidine-2-carboxylic acid Chemical class OC(=O)C1=NC=CC=N1 ZFCHNZDUMIOWFV-UHFFFAOYSA-N 0.000 title abstract 3
- 238000004519 manufacturing process Methods 0.000 title 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 4
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 abstract 3
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 abstract 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 abstract 2
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 abstract 1
- 150000005695 2-halopyrimidines Chemical class 0.000 abstract 1
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 1
- 125000003158 alcohol group Chemical group 0.000 abstract 1
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 229910002091 carbon monoxide Inorganic materials 0.000 abstract 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 239000004009 herbicide Substances 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 abstract 1
- 239000000543 intermediate Substances 0.000 abstract 1
- 229910052763 palladium Inorganic materials 0.000 abstract 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 abstract 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)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Cephalosporin Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
A process is described for preparing 2-pyrimidine-carboxylates of the general formula:
See formula I
wherein R is C1-6-alkyl, C3-6-cycloalkyl, aryl or arylalkyl and R1 to R3, independently of one another, each represent hydrogen, C1-6-alkyl, fluorinated C1-6-alkyl, C1-6-alkoxy, (C1-6-alkoxy) -C1-6-alkyl or (C1-6-alkoxy) carbonyl. The compounds (I) are obtained from the corresponding 2-halopyrimidine, the corresponding alcohol, ROH, and carbon monoxide in the presence of a palladium/phosphine complex and a base. The 2-pyrimidinecarboxylates (I) are intermediates for preparing herbicides.
See formula I
wherein R is C1-6-alkyl, C3-6-cycloalkyl, aryl or arylalkyl and R1 to R3, independently of one another, each represent hydrogen, C1-6-alkyl, fluorinated C1-6-alkyl, C1-6-alkoxy, (C1-6-alkoxy) -C1-6-alkyl or (C1-6-alkoxy) carbonyl. The compounds (I) are obtained from the corresponding 2-halopyrimidine, the corresponding alcohol, ROH, and carbon monoxide in the presence of a palladium/phosphine complex and a base. The 2-pyrimidinecarboxylates (I) are intermediates for preparing herbicides.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1797/96 | 1996-07-18 | ||
| CH179796 | 1996-07-18 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2208900A1 true CA2208900A1 (en) | 1998-01-18 |
| CA2208900C CA2208900C (en) | 2006-08-01 |
Family
ID=4218832
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002208900A Expired - Fee Related CA2208900C (en) | 1996-07-18 | 1997-06-26 | Process for preparing 2-pyrimidinecarboxylates |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US5869667A (en) |
| EP (1) | EP0819679B1 (en) |
| JP (1) | JPH1072451A (en) |
| AT (1) | ATE227275T1 (en) |
| CA (1) | CA2208900C (en) |
| DE (1) | DE59708652D1 (en) |
| DK (1) | DK0819679T3 (en) |
| ES (1) | ES2185842T3 (en) |
| PT (1) | PT819679E (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2001007416A1 (en) * | 1999-07-28 | 2001-02-01 | Lonza Ag | Method of producing pyridazine carboxylic acid derivatives |
| WO2001007415A1 (en) * | 1999-07-28 | 2001-02-01 | Lonza Ag | Method of producing pyridazine-3,6-dicarboxylic acid esters |
| GB9922830D0 (en) | 1999-09-27 | 1999-11-24 | Novartis Ag | Processes |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2341925A1 (en) * | 1973-08-20 | 1975-03-06 | Thomae Gmbh Dr K | 2,4, (opt.5-), 6-substd. pyriminidines as antithrombic agents - e.g. 6-methyl-5-nitro-2-piperazino-4-thiomorpolino-pyrimidine |
| US4622062A (en) * | 1984-02-09 | 1986-11-11 | E. I. Du Pont De Nemours And Company | Herbicidal N-[(4,6-substituted pyrimidin-2-yl)aminocarbonyl]-substituted fused pyrazole-3-sulfonamides |
| JPH0819009B2 (en) * | 1987-03-12 | 1996-02-28 | 日本農薬株式会社 | Method for producing carboxamides |
| DE3826230A1 (en) * | 1988-08-02 | 1990-02-08 | Hoechst Ag | HETEROCYCLIC N-ACYLSUFONAMIDES, METHOD FOR THE PRODUCTION THEREOF, THE AGENTS THEREOF AND THEIR USE AS HERBICIDES OR GROWTH REGULATORS |
| JP3269192B2 (en) * | 1992-08-05 | 2002-03-25 | ロンザ リミテッド | Method for producing 2-halogen-4,6-dialkoxy-pyrimidine |
| JPH0873403A (en) * | 1994-06-30 | 1996-03-19 | Nippon Nohyaku Co Ltd | Method for producing halogen-substituted benzoic acid |
-
1997
- 1997-06-26 CA CA002208900A patent/CA2208900C/en not_active Expired - Fee Related
- 1997-07-04 EP EP97111346A patent/EP0819679B1/en not_active Expired - Lifetime
- 1997-07-04 DK DK97111346T patent/DK0819679T3/en active
- 1997-07-04 AT AT97111346T patent/ATE227275T1/en not_active IP Right Cessation
- 1997-07-04 PT PT97111346T patent/PT819679E/en unknown
- 1997-07-04 ES ES97111346T patent/ES2185842T3/en not_active Expired - Lifetime
- 1997-07-04 DE DE59708652T patent/DE59708652D1/en not_active Expired - Fee Related
- 1997-07-11 JP JP9186947A patent/JPH1072451A/en active Pending
- 1997-07-14 US US08/891,787 patent/US5869667A/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| EP0819679B1 (en) | 2002-11-06 |
| DK0819679T3 (en) | 2003-02-24 |
| EP0819679A2 (en) | 1998-01-21 |
| EP0819679A3 (en) | 1998-01-28 |
| ES2185842T3 (en) | 2003-05-01 |
| US5869667A (en) | 1999-02-09 |
| CA2208900C (en) | 2006-08-01 |
| ATE227275T1 (en) | 2002-11-15 |
| DE59708652D1 (en) | 2002-12-12 |
| PT819679E (en) | 2003-03-31 |
| JPH1072451A (en) | 1998-03-17 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKLA | Lapsed |