Phosphorus oxychloride → 4-Chloro-2-(methylsulfanyl)pyrimidine-5-carbonitrile

Participants

Reaction Steps

A stirred solution of 4-hydroxy-2-(methylthio)pyrimidine-5-carbonitrile (British patent GB901749) (1.00 g, 5.98 mmol) in POCl3 (5 mL) was heated to reflux for 2 h. The reaction mixture was concentrated in vacuo and the residue quenched with ice (100 g). The solution was then basified to pH 8 with sat. aq NaHCO3 and extracted with ethyl acetate (3×50 mL). The combined ethyl acetate layers were washed with water (20 mL), brine (10 mL), dried over Na2SO4, filtered and concentrated to give the title compound.

Provenance & Evidence