Dimethylformamide → HCID 69860012, compound

Participants

Reaction Steps

To a flask containing dry, finely ground potassium carbonate (22.17 g, 0.160 mol) under a nitrogen atmosphere was added anhydrous DMF (800 ml), N-[(2,6-dibromo-4-methoxyphenyl)methyl]-N′-(2,6 dichlorophenyl)-N-[(4-methoxyphenyl)methyl]urea (32.25 g, 0.0535 mol) (INTERMEDIATE 21) and copper iodide (6.80 g, 0.0353 mol). After refluxing one hour the solution was cooled to RT and poured into a solution containing 700 mL NH4OH (28%) and water (8 L). The precipitated product was filtered, washed with water (5×500 mL), hexanes (4×500 mL) and air dried to give 1-(2,6-dichlorophenyl)-3-(4-methoxyphenyl)methyl]-5-bromo-7-methoxy-3,4-dihydro-2(1H)-quinazolinone. 1H NMR(CDCl3, 500 MHz): δ 3.67 (s, 3H), 3.83 (s, 3H), 4.44 (s, 2H), 4.68 (s, 2H), 5.59 (d, 1H, J=2.3 Hz), 674 (d, 1H, J=2.3 Hz), 6.91 (d, 2H, J=8.7 Hz), 7.34-7.37 (m, 3H), 7.50 (d, 2H, J=8.0 Hz), MS(ES) 521 (M+1); LC 1:4.15 min.

Provenance & Evidence