Dimethylformamide → 4-Chloro-6-methoxy-7-(3-(4-methylpiperazin-1-yl)propoxy)quinazoline

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Reaction Steps

A solution of 6-methoxy-7-(3-(4-methylpiperazin-1-yl)propoxy)-3,4-dihydroquinazolin-4-one (2.05 g, 6.2 mmol) in thionyl chloride (30 ml) containing DMF (500 μl) was heated at reflux for 30 minutes. After cooling, the volatiles were removed by evaporation. The residue was partitioned between methylene chloride and saturated aqueous sodium hydrogen carbonate and the aqueous layer was adjusted to pH8 with solid sodium hydrogen carbonate. The organic layer was washed with water, brine, dried (MgSO4) and the volatiles were removed by evaporation. The residue was triturated with ether, collected by filtration, washed with ether and dried under vacuum to give 4-chloro-6-methoxy-7-(3-(4-methylpiperazin-1-yl)propoxy)quinazoline (1.4 g, 65).

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