Water → 7-Benzyloxy-6-methoxy-4-phenoxyquinazoline

HRID 1384529Notes

Reaction equation

[H-].[Na+].[C:3]1([OH:9])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.Cl.[CH2:11]([O:18][C:19]1[CH:28]=[C:27]2[C:22]([C:23](Cl)=[N:24][CH:25]=[N:26]2)=[CH:21][C:20]=1[O:30][CH3:31])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.O>CN1CCCC1=O>[CH2:11]([O:18][C:19]1[CH:28]=[C:27]2[C:22]([C:23]([O:9][C:3]3[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=3)=[N:24][CH:25]=[N:26]2)=[CH:21][C:20]=1[O:30][CH3:31])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

Conditions

Temperature: 110 °C

Procedure

Sodium hydride (400 mg of an 80% suspension in paraffin oil, 13.3 mmol) was added to a solution of phenol (1.26 g, 13.3 mmol) in dry N-methylpyrrolidone (20 ml) and the mixture stirred for 10 minutes. 7-Benzyloxy-4-chloro-6-methoxyquinazoline hydrochloride (1.6 g, 4.7 mmol), (prepared as described for the starting material in Example 1), was then added and the reaction mixture heated at 110° C. for 2 hours. The mixture was allowed to cool, water was added and the mixture extracted with ethyl acetate (3×100 ml). The combined extracts were then washed with 2M sodium hydroxide solution, water and brine. Removal of the solvent under reduced pressure gave 7-benzyloxy-6-methoxy-4-phenoxyquinazoline (1.6 g, 95%) as a yellowish solid. 1H NMR Spectrum: (DMSOd6) 3.98(s, 3H); 5.37(s, 2H); 7.25-7.6(m, 11H); 7.60(s, 1H); 8.54(s, 1H) MS-ESI: 359 [MH]+

Workup

additionwas then added
temperatureto cool
extractionthe mixture extracted with ethyl acetate (3×100 ml)
washThe combined extracts were then washed with 2M sodium hydroxide solution, water and brine
customRemoval of the solvent under reduced pressure

Sources & evidence

ORD record: ord-e4c6e6b4b4ad469884b8acb9d67e97c3
Source dataset: uspto-grants-2001_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06258951B1

Reaction notes

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