Phosphorus oxychloride → 4-Chloro-6-ethoxy-7-methoxyquinazoline

Participants

Reaction Conditions

Reaction Steps

A mixture of 6-(ethyloxy)-7-(methyloxy)-4(1H)-quinazolinone (560 mg, 2.54 mmol) in POCl3 (5 mL, 53.6 mmol) was treated with 1 drop of DMF and heated at 100° C. for 2 hours before being concentrated. The residue was treated with saturated aqueous NaHCO3 and extracted with CH2Cl2. The organic extracts were dried (sodium sulfate) and concentrated to give 4-chloro-6-(ethyloxy)-7-(methyloxy)quinazoline (416 mg, 1.74 mmol, 69%) as an off-white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 8.88 (s, 1 H), 7.46 (s, 1 H), 7.39 (s, 1 H), 4.26 (q, J=6.94 Hz, 2 H), 4.02 (s, 3 H), 1.44 (t, J=7.03 Hz, 3 H). MS (m/z) 239.0 (M+H+).

Provenance & Evidence