4-Chloro-2-(methylsulfanyl)pyrimidine-5-carbonyl chloride → 1-(4-Chloro-2-(methylthio)pyrimidin-5-yl)-2-(2-chlorophenyl)ethanone

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Reaction Conditions

Reaction Steps

An oven dried flask, equipped with stir bar and septa, was charged with 4-chloro-2-(methylthio)pyrimidine-5-carbonyl chloride (Aaron Chemistry, 1338 mg, 6 mmol). The flask was capped with septa, evacuated and backfilled with nitrogen (three times). The solid was dissolved in tetrahydrofuran (24.0 mL), cooled to −78° C. and kept under nitrogen. (2-Chlorobenzyl)magnesium chloride (14.40 mL, 7.20 mmol) was then slowly added. After the addition was completed, the dry ice/acetone bath was removed and the mixture was stirred at ambient temperature for 3 hours. The mixture was quenched with aqueous 1 M HCl (50 mL), extracted with ethyl acetate (3×80 mL) and the combined extracts were washed with brine, dried over magnesium sulfate (MgSO4), filtered and concentrated. The crude product obtained was purified by flash chromatography (Isco®, Redi-Sep® column, 0-30% ethyl acetate/hexane, linear gradient) to afford the title compound. 1H NMR (300 MHz, CDCl3) δ ppm 8.72 (s, 1H), 7.47-7.36 (m, 1H), 7.36-7.21 (m, 3H), 4.41 (s, 2H), 2.61 (s, 3H); MS (ESI) m/z 313 (M+H)+.

Provenance & Evidence