Hydrochloric Acid → 2-[7-(4-Fluoro-benzyloxy)-4-oxo-4H-quinazolin-3-yl]-acetamide

HRID 7627

Reaction equation

[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]=1

Participants

Conditions

Temperature: 140 °C

Procedure

7-(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+).

Workup

temperatureThe resulting suspension was cooled to rt
filtrationThe resulting precipitate was then filtered off
washwashed with water and diethylether
customPartial purification by chromatography on silica gel eluting with ethyl acetate:hexane (2:1)

Sources & evidence

ORD record: ord-02ebb08f2555436889139e7598c8df89
Source dataset: uspto-grants-2006_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07087612B2

Linked notes

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