Methyl cyanoacetate → Methyl cyano[6-(methylthio)-4-pyrimidinyl]acetate

Participants

Reaction Conditions

Reaction Steps

To a suspension of 60% sodium hydride in mineral oil (388 mg, 9.70 mmol) in DMSO (20 mL) was added methyl cyanoacetate (884 mg, 8.92 mmol) at room temperature. After the evolution of hydrogen had ceased, 4-chloro-6-(methylthio)pyrimidine (Intermediate 13, 623 mg, 3.88 mmol) was added. The reaction was heated at 80° C. for 5 hours. The reaction mixtures was then cooled to room temperature and quenched with ice-cooled saturated ammonium chloride solution (50 mL). The solid was filtered and washed with water. Iso-hexane (100 mL) was added to the solid and the resulting mixture was heated at 60° C. for 1 hour and then cooled to room temperature. The solid was filtered and washed with iso-hexane to give the title compound as a yellow solid (700 mg);

Provenance & Evidence