Hydrochloric Acid → 4-(2-Fluoro-5-hydroxy-4-methylanilino)-6-methoxy-7-(4-pyridylmethoxy)quinazoline hydrochloride

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Reaction Steps

A stirred solution of 4-chloro-6-methoxy-7-(4-pyridylmethoxy)quinazoline (35mg, 0.1 mmol) and 2-fluoro-5-hydroxy-4-methylaniline (15 mg, 0.1 mmol) in a mixture of ethereal hydrogen chloride (2 ml) and isopropanol (5 ml) was heated at reflux for 4 hours. The precipitated product was collected by filtration, washed with acetone and dried under vacuum to give 4-(2-fluoro-5-hydroxy-4-methylanilino)-6-methoxy-7-(4-pyridylmethoxy)quinazoline hydrochloride (23mg, 47%). m.p. 257-260° C. 1H NMR Spectrum: (DMSOd6) 2.15(s, 3H); 4.08(s, 3H); 5.60(s, 2H); 6.90(d, 1H); 7.07(d, 1H); 7.47(s, 1H); 7.93(br d, 2H); 8.74(s, 1H); 8.89(br d, 2H); 9.62(br s, 1H); 11.46(s, 1H) MS-ESI: 407 [MH]+

Provenance & Evidence