Triphenylphosphine → 2-[(E)-2-phenylethenyl]-6,7-dihydro-5H-pyrano[2,3-d]pyrimidine

Participants

Reaction Steps

To 5-(3-hydroxypropyl)-2-[(E)-2-phenylethenyl]-4(1H)-pyrimidinone (1.0 g; 4.0 mmol) in THF (20 ml) was added triphenyl phosphine (1.6 g; 6.0 mmol) and diethyl azodicarboxylate (1.0 g; 6.0 mmol). The reaction was allowed to stir at room temperature under nitrogen for 14 hours. The reaction was partitioned between water (20 ml) and EtOAc (100 ml), and the aqueous phase was further extracted with EtOAc (2×50 ml). The combined organic extracts were dried with Na2SO4, the solvents were removed and the crude residue was purified by column chromatography on silica gel using a 0-2.5% MeOH in DCM gradient to provide the desired compound (0.81 g; 84%).

Provenance & Evidence