[F:1][C:2]1[CH:20]=[CH:19][C:5]([CH2:6][O:7][C:8]2[CH:17]=[C:16]3[C:11]([C:12](=[O:18])[NH:13][CH:14]=[N:15]3)=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[H-].[Na+].FC1C=CC(CO)=CC=1.FC1C=C2[C:36]([C:37](=[O:43])[NH:38]C=N2)=CC=1.Cl>CN(C=O)C>[F:1][C:2]1[CH:20]=[CH:19][C:5]([CH2:6][O:7][C:8]2[CH:17]=[C:16]3[C:11]([C:12](=[O:18])[N:13]([CH2:36][C:37]([NH2:38])=[O:43])[CH:14]=[N:15]3)=[CH:10][CH:9]=2)=[CH:4][CH:3]=17-(4-Fluoro-benzyloxy)-3H-quinazolin-4-one: A mixture of sodium hydride (55%, 3.2 g, 73 mmol), 4-fluorobenzyl alcohol (9.2 g, 73 mmol) and 7-fluoro-3H-quinazolin-4-one (3.0 g, 18 mmol) in DMF (75 mL) was heated at 140° C. for 2 h. The resulting suspension was cooled to rt and the mixture acidified to pH 3 with HCl (conc.). The resulting precipitate was then filtered off, washed with water and diethylether. Partial purification by chromatography on silica gel eluting with ethyl acetate:hexane (2:1) afforded the title compound (3.2 g, 66%) as an off-white solid. MS: m/e=271.3 (M+H+).
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