Diethyl Ether → 1-[2-(Methylsulfanyl)pyrimidin-4-yl]ethan-1-one

Participants

Reaction Conditions

Reaction Steps

A solution of methylmagnesium bromide in diethyl ether (3.0 M, 6.10 mL, 18.3 mmol, 3.0 equiv) was added to a solution of N-methoxy-N-methyl-2-(methylthio)pyrimidine-4-carboxamide (1-2, 1.30 g, 6.10 mmol, 1 equiv) in THF at −78° C. The reaction mixture was warmed to 0° C., stirred for 30 minutes, then partitioned between brine and ethyl acetate (2×75 mL). The combined organic layers were dried over sodium sulfate and concentrated to give 1-[2-(methylthio)pyrimidin-4-yl]ethanone (1-3) as a colorless oil. 1H NMR (500 MHz, CDCl3) δ 8.74 (d, 1H, J=4.9 Hz), 7.51 (d, 1H, J=4.9 Hz), 2.70 (s, 3H), 2.63 (s, 3H).

Provenance & Evidence