7-chloro-2-phenoxymethyl-6H-imidazo[1,2-c]pyrimidin-5-one → 2-phenoxymethyl-6H-imidazo[1,2-c]pyrimidin-5-one

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Reaction Steps

10% Palladium hydroxide (0.43 g, 3 mmol) was added to a solution of 7-chloro-2-phenoxymethyl-6H-imidazo[1,2-c]pyrimidin-5-one (0.24 g, 0.85 mmol) and TEA (0.6 mL, 4.32 mmol) in a mixture of AcOEt and MeOH (60 mL). The mixture was hydrogenated in a Parr reactor (45 psi) at 50° C. for 16 hours. Then 10% palladium hydroxide (0.18 g, 0.43 mmol) was added and the mixture hydrogenated again in a Parr reactor (45 psi) at 50° C. for 16 hours. The mixture was hydrogenated over 5 cycles with addition of 10% palladium hydroxide (0.18 g, 0.43 mmol) every cycle. The mixture was filtered through a pad of diatomaceous earth and washed with MeOH. The solvents were evaporated in vacuo and the crude product purified by flash column chromatography (silica; 7 M solution of ammonia in MeOH in DCM with a gradient of 0/100 to 40/60). The desired fractions were collected and the solvents evaporated in vacuo to yield 2-phenoxymethyl-6H-imidazo[1,2-c]pyrimidin-5-one (0.19 g, 92% yield) as a white solid.

Provenance & Evidence