9-Benzyloxy-6-(1-naphthalen-1-yl-cyclopentylmethyl)-2-oxetan-3-yl-3,4-dihydro-2H-pyrazino[1,2-c]pyrimidine-1,8-dione → 9-hydroxy-6-(1-naphthalen-1-yl-cyclopentylmethyl)-2-oxetan-3-yl-3,4-dihydro-2H-pyrazino[1,2-c]pyrimidine-1,8-dione

Participants

Reaction Steps

A solution of 9-benzyloxy-6-(1-naphthalen-1-yl-cyclopentylmethyl)-2-oxetan-3-yl-3,4-dihydro-2H-pyrazino[1,2-c]pyrimidine-1,8-dione (364) (125 mg, 0.23 mmol) in ethanol (60 mL) was degassed under nitrogen, followed by the addition of Pd—C (10%) (40 mg) and again degassed under nitrogen. The reaction mixture was then stirred under a hydrogen atmosphere of balloon pressure for 25 min at room temperature. The reaction mixture was the filtered through a celite bed and the filtrate was concentrated in vacuo to get a crude sticky mass which was purified by preparative TLC plate using as developing solvent 3% methanol in dichloromethane to get pure 9-hydroxy-6-(1-naphthalen-1-yl-cyclopentylmethyl)-2-oxetan-3-yl-3,4-dihydro-2H-pyrazino[1,2-c]pyrimidine-1,8-dione (365) (32 mg, 31%) as an off-white solid.

Provenance & Evidence