Oxalyl chloride → 6-Bromopyrido[2,3-d]pyrimidine-2,4(1H,3H)-dione

Participants

Reaction Steps

Oxalyl chloride (100 mL, 1.16 mmol) was added dropwise to a suspension of 2-amino-5-bromo-nicotinamide (500 mg, 2.31 mmol) in toluene (5 mL) and the resulting mixture was heated to reflux for 4 h. The reaction mixture was cooled and the mustard-colored solid which had formed was collected by filtration. The solid was washed with a small amount of water, MeOH, and then dried under high vacuum (40° C.) overnight to give the title compound (435 mg, 77%): 1H NMR (300 MHz, DMSO-d6) δ 11.86 (s, 1H), 11.60 (s, 1H), 8.72 (d, J=2.5 Hz, 1H), 8.35 (d, J=2.5 Hz, 1H); 13C NMR (126 MHz, DMSO-d6) δ 161.4, 154.8, 151.2, 150.17, 137.8, 112.6, 111.6.

Provenance & Evidence