N-methoxy-N-methyl-2-(methylthio)pyrimidine-4-carboxamide → 1-[2-(Methylthio)pyrimidin-4-yl]-2-phenylethanone

Participants

Reaction Conditions

Reaction Steps

A solution of benzylmagnesium chloride (4.7 mL, 9.38 mmol, 2 equiv) was added to a solution of N-methoxy-N-methyl-2-(methylthio)pyrimidine-4-carboxamide (1–2, 1.0 g, 4.7 mmol, 1 equiv) in THF (25 mL) cooled to −78° C. The reaction solution was allowed to warm to 0° C. and partitioned between ethyl acetate (2×100 mL) and brine. The organic extracts were combined, dried over magnesium sulfate and concentrated. The residue was purified by flash column chromatography. Elution with CH2Cl2 to 15% EtOAc/CH2Cl2 provided 1-[2-(methylthio)pyrimidin-4-yl]-2-phenylethanone (3-1) as a pale yellow solid. 1H NMR (500 MHz, CDCl3) δ 8.73 (d, 1H, J=5 Hz), 7.52 (d, 1H, J=5 Hz), 7.25–7.37 (m, 5H), 4.48 (s, 2H), 2.66 (s, 3H).

Provenance & Evidence