(Diethylamino)sulfur trifluoride → 2-Chloro-5-fluoro-4-(1-fluoro-1-methyl-ethyl)pyrimidine

Participants

Reaction Conditions

Reaction Steps

Diethylaminosulfur trifluoride (6.53 g, 40.5 mmol) is added drop wise to a −78° C. solution of 2-(2-chloro-5-fluoro-pyrimidin-4-yl)propan-2-ol (4.825 g, 25.31 mmol) in dichloromethane (70 mL) under nitrogen. The reaction is stirred at −78° C. for 30 minutes under nitrogen, quenched with saturated aqueous sodium bicarbonate, and warmed to room temperature. The reaction mixture is extracted three times with ethyl acetate. The combined organic layers are dried over sodium sulfate and concentrated under vacuum. The resulting crude product is purified using silica gel column chromatography using a 5-100% gradient of ethyl acetate in hexanes to give the title compound (4.23 g, 87%). ES/MS (m/e): 193 and 195 (M+1).

Provenance & Evidence