Dimethylformamide → HCID 59718927, compound

Participants

Reaction Steps

A 1 L round bottom flask was loaded with sodium hydride dispersion (10.0 g, 250 mmol, 60% in mineral oil) and 200 mL of DMF, and the resulting slurry cooled with an ice bath. Benzotriazole (18.02 g, 151 mmol) was added portionwise over a 10-12 min period. The reaction mixture was stirred for 10 min to allow gas evolution to subside; the ice bath was then removed and 4-chloro-2-methylthiopyrimidine (24.07 g, 150 mmol) was added. The resulting mixture was stirred at RT for 15 minutes, then placed in a 90° C. oil bath for 1.5 hour. The heating bath was turned off and the reaction mixture was allowed to slowly cool with stirring overnight. The reaction mixture was then poured into 500 mL of water and stirred for 20 min, and then filtered. The collected solids were washed with 3 portions of water and 3 portions of a mixture of hexanes/EtOAc (10:1 to 5:1), then dried to give 1-(2-methylsulfanyl-pyrimidin-4-yl)-1H-benzotriazole as an off-white solid (27.05 g, 74% yield), mp=180.5-181.7° C.; MS=244 (M+H)+.

Provenance & Evidence