Imidazole → HCID 12150196, compound

Participants

Reaction Steps

To a suspension of hexane washed NaH (60% in oil, 84 mg, 2.1 mmol) in dry DMF (5 mL) was added imidazole (142 mg, 2.1 mmol). The mixture was stirred at rt for 15 min and was treated with 2-chloroethyl-6,7-methylenedioxy-4-(3,4-methylenedioxyphenyl)quinazoline (232 mg, 0.7 mmol), and then with NaI (105 mg, 0.7 mmol). The mixture was stirred at rt for 15 h and it was poured into ice-water. The precipitated solid was collected by filtration, washed with water, and air dried. The yellow solid was then crystallized from EtOAc to give the title compound as pale yellow needles (101 mg); mp 160-163° C.; 1H NMR (CDCl3) 7.5 (s, 1H), 7.33 (s, 1H), 7.27 (s, 1H), 7.15-7.20 (m, 2H), 6.91-7.05 (m, 3H), 6.15 (s, 2H), 6.08 (s, 2H), 4.60 (m, 2H), 3.53 (m, 2H). Anal. calcd. for C21H16N4O4: C, 64.94; H, 4.15; N, 14.43. Found: C, 64.52; H, 4.11; N, 14.12.

Provenance & Evidence