N-methylpropyn-2-ylamine → 4-[(4-fluoro-2-methyl-1H-indol-5-yl)oxy]-6-methoxy-7-(2-[N-methyl-N-(2-propynyl)amino]ethoxy)quinazoline

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A stirred solution of 7-(2-bromoethoxy)-4-[(4-fluoro-2-methyl-1H-indol-5-yl)oxy]-6-methoxyquinazoline (250 mg, 0.56 mmol), (prepared as described for the starting material in Example 17), in DMF (2.5 ml) was treated with N-methylpropargylamine (116 mg, 1.68 mmol) and stirred at ambient temperature overnight. The solvent was evaporated under vacuum and the residue purified by column chromatography eluting with methylene chloride/methanol (saturated with ammonia) (92/8). The relevant fractions were combined and evaporated under vacuum to give 4-[(4-fluoro-2-methyl-1H-indol-5-yl)oxy]-6-methoxy-7-(2-[N-methyl-N-(2-propynyl)amino]ethoxy)quinazoline as a white solid. (165 mg, 68%).

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