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

HRID 1597218Notes

Reaction equation

[H-].[Na+].[C:3]1([OH:9])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH2:10]([O:17][C:18]1[CH:27]=[C:26]2[C:21]([C:22](Cl)=[N:23][CH:24]=[N:25]2)=[CH:20][C:19]=1[O:29][CH3:30])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.O>CN1CCCC1=O>[CH2:10]([O:17][C:18]1[CH:27]=[C:26]2[C:21]([C:22]([O:9][C:3]3[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=3)=[N:23][CH:24]=[N:25]2)=[CH:20][C:19]=1[O:29][CH3:30])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=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 1-methyl-2-pyrrolidinone (20 ml) and the mixture stirred for 10 minutes. 7-Benzyloxy-4-chloro-6-methoxyquinazoline (1.6 g, 5.3 mmol), 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-methoxy4-phenoxyquinazoline (1.6 g, 84%) as a yellowish solid.

Workup

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-84c88fe8ec0142ac99da01b2db456a93
Source dataset: uspto-grants-2001_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06294532B1

Reaction notes

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