Triphenylphosphine → 9-(benzyloxy)-6-((1-(4-chlorophenyl)cyclopentyl)methyl)-2-phenyl-3,4-dihydro-1H-pyrazino[1,2-c]pyrimidine-1,8(2H)-dione

Participants

Reaction Steps

To a stirred solution of 5-(benzyloxy)-2-((1-(4-chlorophenyl)cyclopentyl)methyl)-6-hydroxy-N-(2-hydroxyethyl)-N-phenylpyrimidine-4-carboxamide (48) (100.1 mg, 179 μmol, Eq: 1.00) in dichloromethane (5 ml) at room temperature was added triphenylphosphine (70.6 mg, 269 μmol, Eq: 1.5) and stirred for 10 min. Then diisopropyl azodicarboxylate (54.4 mg, 52.3 μl, 269 μmol, Eq: 1.5) was added and the reaction mixture was stirred for 18 hrs, concentrated, and chromatographed (silica gel, gradient 0 to 5% methanol-dichloromethane) to obtain 9-(benzyloxy)-6-((1-(4-chlorophenyl)cyclopentyl)methyl)-2-phenyl-3,4-dihydro-1H-pyrazino[1,2-c]pyrimidine-1,8(2H)-dione (49) (white foam, 88.5 mg, 164 μmol, 91.4% yield).

Provenance & Evidence