6-(4-fluoro-phenyl)-2-phenoxymethyl-6H-imidazo[1,2-c]pyrimidin-5-one → 6-(4-fluoro-phenyl)-2-phenoxymethyl-7,8-dihydro-6H-imidazo[1,2-c]pyrimidin-5-one

Participants

Reaction Steps

10% Palladium hydroxide (10 mg, 0.07 mmol) was added to a stirred solution of 6-(4-fluoro-phenyl)-2-phenoxymethyl-6H-imidazo[1,2-c]pyrimidin-5-one (47 mg, 0.14 mmol) in MeOH (50 mL). The mixture was hydrogenated in a Parr reactor at room temperature under H2 atmosphere for 6 hours. Then the mixture was hydrogenated other 7 cycles in a Parr reactor (50 psi) at 50° C. for 16 hours with addition of 10% palladium hydroxide (10 mg, 0.07 mmol) every cycle. The mixture was filtered through a pad of diatomaceous earth and the solvents were evaporated in vacuo. The crude product was purified by flash column chromatography (silica; AcOEt in DCM with a gradient of 0/100 to 50/50). The desired fractions were collected and the solvents evaporated in vacuo to yield 6-(4-fluoro-phenyl)-2-phenoxymethyl-7,8-dihydro-6H-imidazo[1,2-c]pyrimidin-5-one (27 mg, 57% yield) as a white solid. 1H NMR (400 MHz, CDCl3) 8 ppm 3.29 (t, J=6.7 Hz, 2H), 4.00 (t, J=6.7 Hz, 2H), 5.02 (d, J=0.7 Hz, 2H), 6.94-6.99 (m, 1H), 6.99-7.05 (m, 2H), 7.10-7.17 (m, 2H), 7.27-7.35 (m, 4H), 7.57 (s, 1H).

Provenance & Evidence