With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.313339-35-4, name is 4,6-Dichloro-2-(methylthio)pyrimidine-5-carboxylic acid, molecular formula is C6H4Cl2N2O2S, molecular weight is 239.08, as common compound, the synthetic route is as follows.name: 4,6-Dichloro-2-(methylthio)pyrimidine-5-carboxylic acid
Thionyl chloride (1.6 mL, 22.1 mmol) and DMF (0.025 mL) were added to 4,6-dichloro-2-(methylthio)-pyrimidine-5-carboxylic acid (528 mg, 2.21 mmol) obtained in Reference Example 4, and the mixture was stirred at 90C for 4 hours. The mixture was concentrated under reduced pressure, and the residue was dried for 12 hours under reduced pressure. The resulting residue was dissolved in dichloromethane (11 mL), and the mixture was stirred at -78C for 30 minutes after triethylamine (0.25 mL, 1.76 mmol), and a dichloromethane (11 mL) solution of the (S)-2-(aminomethyl)pyrrolidine-1-carboxylic acid tert-butyl ester (295 mg, 1.47 mmol) obtained in Reference Example 6 were added at -78C. Thereafter, a saturated aqueous ammonium chloride solution and ethyl acetate were added to separate the organic layer. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography to give (S)-N-[(1-tert-butoxycarbonylpyrrolidin-2-yl)methyl]-4,6-dichloro-2-methylthiopyrimidine-5-carboxylic acid amide (538 mg, 87%). ESI-MS: m/z 421 [M + H]+. 1H-NMR (CDCl3) delta(ppm): 1.43 (s, 9H), 1.70-2.00 (m, 3H), 2.08 (m, 1H), 2.58 (s, 3H), 3.32-3.46 (m, 3H), 3.60 (m, 1H), 4.10 (m, 1H), 8.24 (brs, 1H).
At the same time, in my other blogs, there are other synthetic methods of this type of compound,313339-35-4, 4,6-Dichloro-2-(methylthio)pyrimidine-5-carboxylic acid, and friends who are interested can also refer to it.
Reference:
Patent; Kyowa Hakko Kirin Co., Ltd.; EP2163554; (2010); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia