[CH:1]1([CH2:4][NH:5][C:6]2[N:15]=[CH:14][C:13]3[C:8](=[CH:9][C:10]([C:17]([O:19]C)=[O:18])=[CH:11][C:12]=3[F:16])[N:7]=2)[CH2:3][CH2:2]1.[Li+].[OH-].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C1COCC1.O>[CH:1]1([CH2:4][NH:5][C:6]2[N:15]=[CH:14][C:13]3[C:8](=[CH:9][C:10]([C:17]([OH:19])=[O:18])=[CH:11][C:12]=3[F:16])[N:7]=2)[CH2:2][CH2:3]1A solution of methyl 2-(cyclopropylmethylamino)-5-fluoro-quinazoline-7-carboxylate (40 mg, 0.15 mmol) in THF (1.3 mL) and water (0.4 mL) was treated with LiOH (10.4 mg, 0.44 mmol) and stirred at ambient temperature for 1 h. The mixture was acidified with 1M aqueous citric acid and the resulting precipitate collected via centrifugation, washed with water, and then dried under high vacuum to afford 2-(cyclopropylmethylamino)-5-fluoroquinazoline-7-carboxylic acid as a yellow solid which was used without further purification.
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