Pyridine → HCID 59648323, compound

Participants

Reaction Steps

Oxalyl chloride (0.98 ml, 11.25 mmol, 1.05 eq) was added dropwise to a stirred solution of 6-[(2,2-Dimethyl-propionyl)-(2-methoxy-ethyl)-amino]-nicotinic acid (3 g, 10.71 mmol) in DCM (30 Ml) at 0° C. followed by one drop of DMF. Stirred at that temperature for 30 min before the addition of 5,6-Diamino-3-cyclopropyl-1-propyl-1H-pyrimidine-2,4-dione (2.4 g, 10.71 mmol, 1 eq) and followed by pyridine (0.866 ml, 10.71 mmol, 1 eq). The reaction mixture was allowed to warm to room temperature for 3 hr then the mixture was evaporated to dryness and redissolved in 30 ml of 4N NaOH. The reaction mixture was heated to reflux for a total of 5 hours. After cooling to room temperature, the pH adjusted with aqueous hydrochloric acid to 7-8. Water was evaporated to half volume then ethanol was added at 0° C. and stirred overnight (15 hr). The reaction mixture is filtered and the solid was washed with water and then ethanol. The product is then dried at 50° C. to provide 3.41 g (83%). 1H NMR (400 MHz, DMSO-d6) δ 13.68 (1H), 8.7 (1H), 8.0 (1H), 7.15 (1H), 6.6 (1H), 3.95 (2H), 3.48 (4H), 3.26 (3H), 2.6 (1H), 1.7 (2H), 1.05 (2H), 0.9 (3H), 0.7 (2H); m/z (ES+) 385.44

Provenance & Evidence