3-(benzyloxy)-5-(biphenyl-3-yl)-1-methylpyridin-2(1H)-one → 5-Biphenyl-3-yl-3-hydroxy-1-methylpyridin-2(1H)-one

Participants

Reaction Steps

A solution of 3-(benzyloxy)-5-(biphenyl-3-yl)-1-methylpyridin-2(1H)-one (34 mg, 0.093 mmol) in MeOH (5 mL) was hydrogenated under atmospheric H2 in the presence of 5% Pd/C (15 mg) for 21 h. Filtered and concentrated. Purification by preparative HPLC (5-65% CH3CN/H2O over 20 min, 0.05% added TFA) afforded 2.5 mg (10%) of 5-Biphenyl-3-yl-3-hydroxy-1-methylpyridin-2(1H)-one as a white solid. 1H NMR (500 MHz, CDCl3): δ 7.63-7.60 (m, 3H), 7.56 (d, J=7.8 Hz, 1H), 7.52-7.43 (m, 3H), 7.41-7.36 (m, 2H), 7.25-7.06 (br, 2H), 3.72 (s, 3H). High resolution mass spec (FT/ICR) cale (M+H)+=278.1165 found 278.1176.

Provenance & Evidence