Benzyl ((4-oxo-4,5,7,8-tetrahydro-3H-pyrano[4,3-D]pyrimidin-2-YL)methyl)carbamate → 2-(Aminomethyl)-7,8-dihydro-3H-pyrano[4,3-D]pyrimidin-4(5H)-one

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Reaction Steps

A solution of benzyl (4-oxo-4,5,7,8-tetrahydro-3H-pyrano[4,3-d]pyrimidin-2-yl)methylcarbamate (55.5 g, 176 mmol) in methanol (4 L) was degassed several times under nitrogen then palladium on carbon (1.87 g, 1.76 mmol, 10% on carbon) was added slowly under nitrogen atmosphere. The mixture was stirred under a hydrogen balloon at ambient temperature until TLC showed complete consumption of starting material. Filtration through a pad of Celite and evaporation of solvent provided the title compound (32 g, >99% yield). 1H NMR (400 MHz, CD3OD) δ 4.49 (s, 2H), 3.93 (t, J=5.5 Hz, 2H), 3.77 (s, 2H), 2.66 (t, J=5.5 Hz, 2H). MS m/z 182.2 (M+1), retention time=0.39 min.

Provenance & Evidence