Ethanol → HCID 178467012, compound

Participants

Reaction Steps

A mixture of [5-hydroxy-7-(methyloxy)-4-oxo-3(4H)-quinazolinyl]methyl 2,2-dimethylpropanoate (1 g, 3.26 mmol, prepared according to J. Med. Chem. (2006) 49 6465), triphenylphosphine (1.370 g, 5.22 mmol), and ethanol (0.210 mL, 3.59 mmol) in DCM (10 mL) at 0° C. was treated dropwise over 2 minutes with a 40% solution of DEAD in toluene (2.379 mL, 5.22 mmol). After addition, the mixture was warmed to room temperature and stirred for 3 hours before being concentrated. The residue was dissolved in 7 M ammonia in methanol (10 mL, 70.0 mmol) and the mixture was stirred for 3 days. The solid was collected by filtration and washed with MeOH and CH2Cl2 to give 5-(ethyloxy)-7-(methyloxy)-4(1H)-quinazolinone (286 mg, 40%) as a white solid. MS (m/z) 221.1 (M+H+).

Provenance & Evidence