Acetonitrile → 8-Amino-2,3-dimethylimidazo[1,2-a]pyridine-6-carboxamide

Participants

Reaction Steps

5,6-Diaminonicotinamide (12.5 g, 82 mmol), 3-bromo-2-butanon (13.6, 90 mmol) and acetonitrile (150 ml) were refluxed for 20 h. Additional 3-bromo-2-butanon (4.0 g, 26.5 mmol) was added and the reaction mixture was refluxed for 5 h. Upon cooling the solids were removed by filtration. The solids were added to methylene chloride (150 ml), methanol (150 ml) and potassium carbonate (22 g, 160 mmol) and were stirred for 30 min. The solids were removed by filtration and evaporation of the solvents under reduced pressure gave an oily residue. Purification by column chromatography on silica gel eluting with methylene chloride:methanol (5:1) gave 3.3 g (20%) of the title compound.

Provenance & Evidence