Methanol → 9-benzyloxy-2-methyl-6-(1-pyridin-2-yl-cyclopentylmethyl)-3,4-dihydro-2H-pyrazino[1,2-c]pyrimidine-1,8-dione

Participants

Reaction Steps

To a stirred solution of 5-benzyloxy-6-hydroxy-2-(1-pyridin-2-yl-cyclopentylmethyl)-pyrimidine-4-carboxylic acid (2-hydroxyethyl)-methyl-amide (443) (90 mg, 0.195 mmol), in dichloromethane (10 mL), TPP (178.64 mg, 0.682 mmol) and diisopropyl azodicarboxylate (0.115 mL, 0.584 mmol) were added and stirring was continued for 1 h at room temperature while silica thin layer chromatography was performed (3% methanol in ethyl acetate; Rf=0.2). After completion of the reaction, water (5 mL) was added and the mixture was extracted with dichloromethane (2×30 mL). The organic part was dried and concentrated. The resulting crude product was purified by normal silica gel (100-200 mesh) column chromatography using 60-70% ethyl acetate in hexane as gradient polarity mobile phase to get 9-benzyloxy-2-methyl-6-(1-pyridin-2-yl-cyclopentylmethyl)-3,4-dihydro-2H-pyrazino[1,2-c]pyrimidine-1,8-dione (444) (71 mg, 82%) as a white solid.

Provenance & Evidence