Triphenylphosphine → 4-Chloro-7-(3-chloropropoxy)-6-methoxyquinazoline

Participants

Reaction Steps

Triphenylphosphine (2.6 g, 10.1 mmol) and 3-chloropropanol (0.69 ml, 8.2 mmol) were added to a suspension of 4-chloro-7-hydroxy-6-methoxyquinazoline (1.65 g, 7.8 mmol) in dichloromethane (100 ml) under argon. The flask was placed in a water bath at 20° C. and di-tertbutyl azodicarboxylate (2.30 g, 10.1 mmol) added portion wise over a few minutes. The reaction mixture was stirred at ambient temperature for 2 hours. The reaction mixture was concentrated and the solution loaded directly onto a silica chromatography column. Elution with ethyl acetate:petroleum ether (3:7), yielded 4-chloro-7-(3-chloropropoxy)-6-methoxyquinazoline (2.0 g, 91% yield):

Provenance & Evidence