Phosphorus oxychloride → tert-butyl (2R)-2-({[7-(benzyloxy)-4-chloroquinazolin-5-yl]oxy}methyl)pyrrolidine-1-carboxylate

Participants

Reaction Conditions

Reaction Steps

Phosphorous oxychloride (520 μl) was added dropwise to a mixture of tert-butyl (2R)-2-({[7-(benzyloxy)-4-oxo-3,4-dihydroquinazolin-5-yl]oxy}methyl)pyrrolidine-1-carboxylate (500 mg) and N,N-diisopropylethylamine (52 μl) in DCM (10 ml) and the reaction mixture was heated at 50° C. for 62 hours. The reaction mixture was concentrated in vacuo and then water and saturated aqueous sodium carbonate (cooled to 4° C.) was added. The aqueous mixture was then extracted with DCM and the organic layer was dried (MgSO4) and concentrated in vacuo to leave tert-butyl (2R)-2-({[7-(benzyloxy)-4-chloroquinazolin-5-yl]oxy}methyl)pyrrolidine-1-carboxylate as a brown oil, which was used without further purification.

Provenance & Evidence