Acetonitrile → HCID 67282590, compound

Participants

Reaction Steps

Into a round-bottom flask was added ethyl 4-oxo-3,4-dihydroquinazoline-6-carboxylate (0.14 g, 0.63 mmol), 3-bromobenzyl bromide (0.24 g, 0.95 mmol), cesium carbonate (0.25 g, 0.76 mmol), acetonitrile (12 mL) and DMF (3 mL). The reaction mixture was stirred at rt for 16 h. The mixture was then concentrated and to the residue was added EtOAc and water. After separation, the aqueous phase was extracted with EtOAc (2×). The combined organic phases were then washed with brine, dried over anhydrous Na2SO4, filtered and concentrated. Flash column chromatography (25% to 50% EtOAc/hexanes) afforded ethyl 3-(3-bromobenzyl)-4-oxo-3,4-dihydroquinazoline-6-carboxylate (0.17 g, 68%) as a white solid. LC-MS: (FA) ES+ 388; 1H NMR (CDCl3, 300 MHz) δ 9.00 (d, J=1.70 Hz, 1H), 8.39 (dd, J=8.5, 1.9 Hz, 1H), 8.26 (s, 1H), 7.76 (d, J=8.5 Hz, 1H), 7.52 (s, 1H), 7.46 (d, J=7.7 Hz, 1H), 7.26 (m, 2H), 5.17 (s, 2H), 4.42 (q, J=7.2 Hz, 2H), 1.42 (t, J=7.0 Hz, 3H).

Provenance & Evidence