N-(5-methylpyrazin-2-yl)-3-[(phenylmethyl)oxy]-5-[(3S)-tetrahydrofuran-3-yloxy]benzamide → 3-Hydroxy-N-(5-methylpyrazin-2-yl)-5-[(3S)-tetrahydrofuran-3-yloxy]benzamide

Participants

Reaction Steps

10% Palladium on charcoal (500 mg) was added to a solution of N-(5-methylpyrazin-2-yl)-3-[(phenylmethyl)oxy]-5-[(3S)-tetrahydrofuran-3-yloxy]benzamide (5.0 g, 12.34 mmol) in ethanol (50 mL) and THF (100 mL) and the mixture stirred under an atmosphere of hydrogen at RT for 16 hours. The mixture was filtered through Celite®, the solvents evaporated in vacuo to a residue which was crystallised from ethyl acetate to give the desired material (3.6 g). 1H NMR δ (d6-DMSO): 2.0 (m, 1H), 2.25 (m, 1H), 2.5 (s, 3H), 3.75-3.95 (m, 4H), 5.1 (m, 1H), 6.5 (d, 1H), 7.0 (d, 1H), 7.05 (d, 1H), 8.35 (s, 1H), 9.25 (s, 1H), 9.75 (s, 1H), 10.8 (s, 1H); m/z 316 (M+H)+.

Provenance & Evidence