Dimethylformamide → 4-(2,4-Difluoro-5-hydroxyanilino)-6-methoxy-7-(2-methoxyethoxy)quinazoline hydrochloride

Participants

Reaction Steps

6-Methoxy-7-(2-methoxyethoxy)-3,4-dihydroquinazolin-4-one (200 mg, 0.8 mmol), (prepared as described for the starting material in Example 9), and DMF (0.1 ml) in thionyl chloride (20 ml) were heated at reflux for 2 hours. Excess thionyl chloride was removed by evaporation and the residue azeotroped with toluene. The residue was dissolved in isopropranol (15 ml), 2,4-difluoro-5-hydroxyaniline (128 mg, 0.88 mmol), (prepared as described for the starting material in Example 11), added, and the mixture heated at reflux for 2 hours. The reaction mixture was then allowed to cool, the precipitated product collected by filtration, washed with isopropanol and dried to give 4-(2,4-difluoro-5-hydroxyanilino)-6-methoxy-7-(2-methoxyethoxy)quinazoline hydrochloride (83 mg, 28%).

Provenance & Evidence