Methanol → 2-[(4-fluorophenyl)-hydroxymethyl]-7-methyl-1H-quinazolin-4-one

HRID 625761

Reaction equation

[NH2:1][C:2]1[CH:10]=[C:9]([CH3:11])[CH:8]=[CH:7][C:3]=1[C:4]([NH2:6])=[O:5].[F:12][C:13]1[CH:18]=[CH:17][C:16]([CH:19]2[O:23]C(=O)O[C:20]2=O)=[CH:15][CH:14]=1.C[O-].[Na+].CO>C1COCC1>[F:12][C:13]1[CH:18]=[CH:17][C:16]([CH:19]([C:20]2[N:6]=[C:4]([OH:5])[C:3]3[C:2](=[CH:10][C:9]([CH3:11])=[CH:8][CH:7]=3)[N:1]=2)[OH:23])=[CH:15][CH:14]=1

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of 2-amino-4-methylbenzamide (3 g, 20.0 mmol) in THF (40 mL) was added 5-(4-fluorophenyl)-1,3-dioxolane-2,4-dione from Example 16 (4.7 g, 24 mmol) and the solution was stirred for 2 h at 50° C. Sodium methoxide in MeOH (25%, 5.2 mL, 24 mmol) was then added and the solution was stirred at 50° C. overnight. The reaction mixture solution was concentrated, 2N HCl was added and the mixture was filtered. The collected solid was dried to give 2-(((4-fluorophenyl)(hydroxy)methyl)-7-methylquinazolin-4-ol (5.14 g, 91%) which was used without further purification. LC-MS (ESI) m/z 285 (M+H)+.

Workup

stirringthe solution was stirred at 50° C. overnight
concentrationThe reaction mixture solution was concentrated
addition2N HCl was added
filtrationthe mixture was filtered
customThe collected solid was dried

Sources & evidence

ORD record: ord-4b4408a992bb4972b29016de0773ca8e
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09308207B2

Linked notes

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