Diethyl Ether → 2-(2-Chloro-5-fluoropyrimidin-4-yl)propan-2-ol

Participants

Reaction Conditions

Reaction Steps

To a stirred, −78° C. solution of 1-(2-chloro-5-fluoro-pyrimidin-4-yl)ethanone (10.06 g, 57.6 mmol) in tetrahydrofuran (100 mL) under nitrogen is added methyl magnesium bromide in diethyl ether (3 M, 124 mL, 72.04 mmol) and the resulting mixture is stirred at −78° C. for 20 minutes. The reaction is quenched with aqueous saturated ammonium chloride and the mixture is 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 crude product is purified using silica gel column chromatography using a 5-100% gradient of ethyl acetate in hexanes to give the title compound (7.06 g, 64%). ES/MS (m/e): 191 and 193 (M+1).

Provenance & Evidence