Chloroacetonitrile → 3-Amino-4,6-dimethylthieno[2,3-b]pyridine-2-carbonitrile

Participants

Reaction Steps

The 3-cyano-4,6-dimethyl-2-mercaptopyridine (500 mg, 3.04 mmol) was stirred in DMF (6.0 mL). An aqueous 10% KOH solution (1.71 mL, 3.04 mmol) was added, followed by chloroacetonitrile (0.19 mL, 3.04 mmol). The reaction was stirred at RT for 15 minutes, LC/MS indicates initial thio-alkylation is complete. A second equivalent of 10% KOH (1.71 mL, 3.04 mmol) was added and the resulting slurry was warmed to 50° C. and stirred about 30 min. LC/MS indicates reaction is done. The slurry was cooled to RT, then poured into 80 g of crushed ice and allowed to warm until the ice melted. The cold slurry was poured through filter paper, washing the solid with cold water. The solid was collected and dried in a vacuum oven to give 580 mg (94%) of the pure product as a light yellow solid. 1H NMR (400 MHz, DMSO-d6): δ ppm 7.09 (s, 1H), 6.50 (s, 2H), 2.70 (s, 3H), 2.49 (s, 3H). LC/MS: RT=0.56 min., m/z=204.0 [M+H]+.

Provenance & Evidence