Ethyl orthoformate → 6-Chloropyrido[3,2-d]pyrimidin-4(3H)-one

Participants

Reaction Steps

A suspension of 3-amino-6-chloropicolinamide (2.56 g, 14.9 mmol) in triethylorthoformate (45 mL, 271 mmol) was refluxed for 6 h. The reaction mixture was cooled to room temperature, diluted with hexane, and then filtered. The filter cake was washed with hexane and dried under vacuum to give 6-chloropyrido[3,2-d]pyrimidin-4(3H)-one (2.55 g, 94%) as a pale yellow solid. 1H-NMR (DMSO-d6, Varian 400 MHz) δ 7.88 (1H, d, J=8.4 Hz), 8.14 (1H, d, J=8.4 Hz), 8.20 (1H, s), 12.65 (1H, brs). m/z=182.06 [M+1]+.

Provenance & Evidence