Ammonium formate → Methyl 3-(pyrimidin-5-yl)propanoate

Participants

Reaction Conditions

Reaction Steps

To a solution of methyl 3-(5-pyrimidyl)acrylate (85 g) in glacial acetic acid was added 10% palladium on charcoal (11.3 g) and ammonium formate (74.2 g) under argon. The mixture was heated at 110° C. for 20 min, cooled and the solvent removed in vacuo. The resulting oil was dissolved in dichloromethane (1.5 L) and washed with saturated sodium bicarbonate (750 ml). The aqueous layer was extracted with further dichloromethane (200 ml), the organic layers were combined and dried over magnesium sulfate. Removal of the solvent under reduced pressure gave an oil. This was distilled under reduced pressure to give methyl 3-(5-pyrimidyl)propionate (26 g). 1H-NMR (CDCl3) δ 2.69(2H, t), 2.97(2H, t), 3.70(3H, s), 8.65(2H, s) and 9.12(1H, s).

Provenance & Evidence