2-Pyridone → 3-Bromo-1-methyl-5-(pyrimidin-4-yl)pyridin-2(1H)-one

Participants

Reaction Conditions

Reaction Steps

20 g of 3-bromo-5-(4-pyrimidyl)-2(1H)-pyridone are suspended in 200 ml of dimethylformamide. A solution of 4.6 g of sodium methoxide in 300 ml of dry dimethylformamide and 15 ml of methanol is added to the pyridone suspension with stirring. The reaction mixture is filtered, 5.3 ml of methyl iodide are added to the filtrate and the mixture heated to 60° C. for 2 hours. After cooling to RT, the solution is concentrated in vacuo resulting in a liquid residue which crystallizes out upon addition of distilled H2O. The solid is stirred with 400 ml of distilled H2O, filtered, washed with H2O, isopropyl alcohol, and ether and dried, yielding 3-bromo-1-methyl-5-(4-pyrimidyl)-2-pyridone, M.P. 208°-210° C.

Provenance & Evidence