1-Bromo-3-chloropropane → 2-[2-(3-chloro-4-fluorophenyl)-6-(3-chloropropoxy)-4-oxo-4H-quinazolin-3-yl]-N-isopropylacetamide

Participants

Reaction Steps

A mixture of 2-[2-(3-chloro-4-fluorophenyl)-6-hydroxy-4-oxo-4H-quinazolin-3-yl]-N-isopropylacetamide (INTERMEDIATE IV.1) (373 mg, 0.96 mmol), 3-bromo-1-chloropropane (0.28 mL, 2.87 mmol) and K2CO3 (662 mg, 4.80 mmol) in acetonitrile (5 mL) was heated at reflux temperature for 24 h. The mixture was cooled to room temperature and then poured into ice water (40 mL). The resultant white solid was collected by filtration and washed with additional portions of cold water (3×20 mL) followed by washing with cold diethyl ether (3×10 mL) and cold hexane (2×10 mL) to remove residual 3-bromo-1-chloropropane. In this way 2-[2-(3-chloro-4-fluorophenyl)-6-(3-chloropropoxy)-4-oxo-4H-quinazolin-3-yl]-N-isopropylacetamide (391 mg, 0.84 mmol, 87%) was obtained.

Provenance & Evidence