Triethylamine → N-{4-[(3-bromophenyl)amino]pyrido[3,4-d]pyrimidin-6-yl}prop-2-enamide

Participants

Reaction Steps

To a solution of 6-amino-4-[(3-bromophenyl)amino]pyrido[3,4-d]pyrimidine (J Med Chem, 1996;39:1823) (455 mg, 1.50 mmol) in dry THF (50 mL) at 0° C. under N2 was added Et3N (22.5 mmol, 1.61 mL), a catalytic amount of DMAP (45 mg) and acryloyl chloride (4.50 mmol, 366 μL). The reaction mixture was stirred for 1 hour and then additional acryloyl chloride (100 μL) was added and the reaction was allowed to warm to room temperature and stirred for another hour before being worked up as in the previous example, to give after column chromatography on silica gel eluting with MeOH/EtOAc (5:95), N-[4-[(3-bromophenyl)amino]pyrido[3,4-d]pyrimidin-6-yl]acrylamide (20 mg, 37%) as a cream powder, mp (EtOAc/MeOH) 238-245° C. (dec.).

Provenance & Evidence