1-Bromo-3-chloropropane → HCID 66918992, compound

Participants

Reaction Steps

N-Cyclopropyl-3-(6-hydroxy-4-oxoquinazolin-3(4H)-yl)-4-methylbenzamide (5 g), 1-bromo-3-chloropropane (7.4 ml) and potassium carbonate (20.6 g) were stirred in DMF (175 ml) at 50° C. for 24 hours. The reaction mixture was diluted with ethyl acetate and washed with water (5×), brine (2×), dried (magnesium sulfate) and concentrated. Purification by column chromatography on a silica column eluting with 70-80% ethyl acetate/hexane gave 3-[6-(2-chloropropoxy)-4-oxoquinazolin-3(4H)-yl]-N-cyclopropyl-4-methylbenzamide (3.28 g) as a white solid; NMR Spectrum: (DMSOd6) 0.56 (m, 2H), 0.69 (m, 2H), 2.14 (s, 3H), 2.22 (m, 2H), 2.85 (m, 1H), 3.81 (t, 2H), 4.23 (m, 2H), 7.52 (m, 2H), 7.60 (s, 1H), 7.74 (d, 1H), 7.84 (s, 1H), 7.90 (d, 1H), 8.20 (s, 1H), 8.43 (d, 1H); Mass Spectrum: M+H+ 412.

Provenance & Evidence