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| | methyl 6-chloropyrimidine-4-carboxylate Basic information |
| Product Name: | methyl 6-chloropyrimidine-4-carboxylate | | Synonyms: | 4-PyriMidinecarboxylic acid, 6-chloro-, Methyl ester;methyl 6-chloropyrimidine-4-carboxylate;Methyl 6-chloro-4-pyrimidinecarboxylate;NSC 58346;methyl 6-chloropyrimidine-4-carboxylate ISO 9001：2015 REACH;4-Pyrimidinecarboxylic acid, 6-chloro-, methyl ester (7CI, 9CI, ACI);6-chloro-4-Pyrimidinecarboxylic acid methyl ester (7CI 9CI ACI);6-Chloropyrimidin-4-carboxylic acid methyl ester (7CI 9CI aci) | | CAS: | 6627-22-1 | | MF: | C6H5ClN2O2 | | MW: | 172.57 | | EINECS: | | | Product Categories: | | | Mol File: | 6627-22-1.mol |  |
| | methyl 6-chloropyrimidine-4-carboxylate Chemical Properties |
| Boiling point | 271℃ | | density | 1.372 | | Fp | 118℃ | | storage temp. | under inert gas (nitrogen or Argon) at 2-8°C | | pka | -2.89±0.17(Predicted) | | Appearance | Light yellow to brown Solid | | InChI | InChI=1S/C6H5ClN2O2/c1-11-6(10)4-2-5(7)9-3-8-4/h2-3H,1H3 | | InChIKey | IAEUEOUJKNGPMO-UHFFFAOYSA-N | | SMILES | C1=NC(Cl)=CC(C(OC)=O)=N1 |
| | methyl 6-chloropyrimidine-4-carboxylate Usage And Synthesis |
| Synthesis | General procedure for the synthesis of methyl 6-chloropyrimidine-4-carboxylate from methyl 6-oxo-3,6-dihydropyrimidine-4-carboxylate: [0778] To a 2000 mL four-necked round-bottomed flask was added methyl 6-hydroxypyrimidine-4-carboxylate (115 g, 746.16 mmol, 1.00 equiv.), acetonitrile (1,200 mL), and phosphorous triclopyr (340 g, 2.22 mol, 3.00 equiv). The reaction mixture was stirred at 80 °C overnight. Upon completion of the reaction, the mixture was cooled to room temperature and concentrated under vacuum. Subsequently, the reaction mixture was diluted with 1000 mL of ethyl acetate and quenched with 1000 mL of ice water. The aqueous phase was extracted with 3 x 500 mL of ethyl acetate. The organic layers were combined, washed sequentially with 1000 mL of water and 1000 mL of saturated saline, dried over anhydrous sodium sulfate, and concentrated under vacuum. The residue was purified by silica gel column chromatography using ethyl acetate/petroleum ether (1:4) as eluent to give 76 g (59% yield) of methyl 6-chloropyrimidine-4-carboxylate as a white solid.LCMS [M + H]+ 173. | | References | [1] Patent: WO2016/128529, 2016, A1. Location in patent: Paragraph 0774; 0777; 0778
[2] Patent: WO2018/15410, 2018, A1. Location in patent: Paragraph 0228; 0232-0233 |
| | methyl 6-chloropyrimidine-4-carboxylate Preparation Products And Raw materials |
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