Sodium hydride → HCID 22288424, compound

Participants

Reaction Conditions

Reaction Steps

2-Phenylimidazole (1-2, 50 g, 347 mmol) was dissolved in 400 ml DMF and the resulting solution was cooled to 0° C. Sodium hydride (8.32 g of solid NaH, plus 13.9 g of a 60% dispersion in mineral oil, 347 mmol) was added and the mixture was stirred for 10 minutes. 4-Chloro-2-(methylthio)pyrimidine (1-1, 55.7 g, 347 mmol) was then added over 2 minutes. The reaction was then heated to 100° C. After stirring overnight the reaction was partitioned between water and EtOAc. The organic phase was washed 2× with water, dried over Na2SO4, filtered and concentrated. Purification by flash column chromatography (eluting with 50:50 to 70:30 EtOAc/Hexane) afforded 2-(methylthio)-4-(2-phenyl-1H-imidazol-1-yl)pyrimidine.

Provenance & Evidence