2-Chlorobenzoyl chloride → HCID 86642733, compound

Participants

Reaction Conditions

Reaction Steps

Dissolve 6-chloro-2-methyl-N*4*-(tetrahydro-2H-pyran-4-yl)-pyrimidine-4,5-diamine (24.4 g, 100.4 mmol) in dimethylacetamide (175 mL) in a 500 mL 3-necked flask under a nitrogen atmosphere. Cool the resulting solution to 0-5° C. Via addition funnel, add 2-chlorobenzoyl chloride (15.5 mL, 122.4 mmol) over 20 minutes, maintaining the internal temperature below 10° C. Rinse the addition funnel with dimethylacetamide (1.0 mL). Allow the resulting mixture to stir overnight while self-warming to ambient temperature. Charge ice cold de-ionized water (250 mL) to a second 500 mL flask and then transfer the reaction mixture into the cold water over 20 minutes. Stir the resulting slurry for 2 hours. Filter the solids, wash with cold water (120 mL)) and vacuum dry overnight at 50° C. to afford 2-chloro-N-(4-chloro-2-methyl-6-(tetrahydro-2H-pyran-4-ylamino)-pyrimidin-5-yl) benzamide as an off-white solid (33.1 g). MS (m/z): 381/382 (M+1).

Provenance & Evidence