Methanol → 9-benzyloxy-2-isopropyl-6-(4-oxo-1-phenyl-cyclohexylmethyl)-3,4-dihydro-2H-pyrazino[1,2-c]pyrimidine-1,8-dione

Participants

Reaction Steps

To a solution of 5-benzyloxy-6-hydroxy-2-(4-oxo-1-phenyl-cyclohexylmethyl)-pyrimidine-4-carboxylic acid (2-hydroxyethyl)-isopropylamide (272) (200 mg, 0.39 mmol) in dichloromethane (25.0 mL) was added triphenyl phosphine (152 mg, 0.58 mmol) and diisopropyl azodicarboxylate (0.12 mL, 0.58 mmol) at room temperature and stirred for 30 min (silica TLC, 5% methanol in ethyl acetate, Rf=0.5). The reaction mixture was concentrated under reduced pressure and purified by normal silica gel (100-200 mesh) column chromatography using gradient polarity mobile phase (50% ethyl acetate in hexane to 5% methanol in dichloromethane) to get pure 9-benzyloxy-2-isopropyl-6-(4-oxo-1-phenyl-cyclohexylmethyl)-3,4-dihydro-2H-pyrazino[1,2-c]pyrimidine-1,8-dione (273) (140 mg, 72.53%) as a white solid.

Provenance & Evidence