Triethylamine → 4-(3'-Bromo-4'-hydroxylphenyl)-amino-6,7-dimethoxy-quinazoline

Participants

Reaction Steps

A mixture of 448 mg (2 mmol) of 4-chloro-6,7-dimethoxy-quioazoline (7) and 2.5 mmol of 3-bromo-4-hydroxyaniline in 20 ml of alcohol (EtOH or MeOH) was refluxed for 8 hours. After cooling, triethylamine was added to basify the solution, and the solvent was concentrated to give material that was recrystallized from DMF to give compound (2); 89.90%; m.p. 233.0-233.5° C.; 1H NMR(DMSO-d6): δ 10.08(s, 1H, —NH), 9.38(s, 1H, —OH), 8.40(s, 1H, 2-H), 7.89(d, 1H, J2′,5′=2.7 Hz, 2′-H), 7.75(s, 1H, 5-H), 7.55(dd, 1 H, J5′,6′=9.0 Hz, J2′,6′=2.7 Hz, 6′-H), 7.14(s, 1H, 8-H), 6.97(d, 1H, J5′,6′=9.0 Hz, 5′-H), 3.92(s, 3H, —OCHER), 3.90(s, 3H, —OCH3). UV(MeOH)λmax(e): 203.0, 222.0, 250.0, 335.0 nm. IR(KBr)umax: 3431(br), 2841, 1624, 1498, 1423, 1244 cm−1. GC/MS m/z 378( M+ +2, 90.68), 377(M+ +1,37.49), 376(M+, 100.00), 360(M+3.63), 298(18.86), 282 (6.65).

Provenance & Evidence