3-(benzyloxy)-N-cyclobutyl-1,6-dimethyl-4-oxo-1,4-dihydropyridine-2-carboxamide → N-cyclobutyl-3-hydroxy-1,6-dimethyl-4-oxo-1,4-dihydropyridine-2-carboxamide

Participants

Reaction Steps

A mixture of N-cyclobutyl-3-benzyloxy-1,6-dimethyl-4-oxo-1,4-dihydropyridine-2-carboxamide (1.528 g, 4.68 mmol, 1.0 equiv), 10% Pd on activated carbon (200 mg, wet), and ethanol (200 ml) was stirred under 50 psi of H2 at room temperature for 2.5 h. The catalyst was filtered through Celite® and the filtrate was evaporated to give a solid, which was recrystallized from MeOH gave the titled compound (0.57 g, 51.5%) as a white solid. M.p. 277.3° C. (dec); 1H-NMR (DMSO-d6, 400 MHz) δ 1.68-1.70 (m, 2H, cyclobutyl H), 1.95-2.01 (m, 2H, cyclobutyl H), 2.20-2.26 (m, 2H, cyclobutyl H), 2.29 (s, 3H, CH3), 3.41 (s, 3H, NCH3), 4.31-4.35 (m, 1H, CH), 6.13 (s, 1H, CH), 8.98 (br, 1H, NH); MS (m/z) 237 (M++1), 185, 166, 123.

Provenance & Evidence