Potassium Carbonate → 4-(4-Chloro2-fluoroanilino)-7-(3-ethoxycarbonylpropoxy)6-methoxyquinazoline

Participants

Reaction Conditions

Reaction Steps

Ethyl 4chlorobutyrate (0.154 ml, 1.1 mmol) was added to a mixture of 4{4-chloro-2-fluoroanilino)7-hydroxy-6-methoxyquinazoline (319.5 mg, 1 mmol), (prepared as described for the starting material in Example 2), and anhydrous potassium carbonate (690 mg, 5 mmol) in DMF (10 ml). The mixture was stirred and heated at 105° C. for 4 hours then allowed to cool. The mixture was diluted with methylene chloride and the insolubles were removed by 110 filtration. The solvent was removed from the filtrate by evaporation and the residue was purified by column chromatography eluting with methylene chloride/methanol/aqueous ammonia (100/8/1). The purified product was triturated with ether collected by filtration and dried to give 4-(4-chloro-2-fluoroanilino)-7-(3-ethoxycarbonylpropoxy)-6-methoxyquinazoline (230 mg, 53%). 1H NMR Spectrum: (DMSOd6) 1.18(t, 3H); 2.02(m, 2H); 2.48(hi, 2H); 3.94(s, 3H); 4.06(q, MS-ESI: 434 [MH]+

Provenance & Evidence