Potassium Carbonate → Methyl 4-oxo-3-[3-(trifluoromethyl)benzyl]-3,4-dihydroquinazoline-6-carboxylate

HRID 1616109Notes

Reaction equation

[O:1]=[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:12]([O:14][CH3:15])=[O:13])[CH:10]=2)[N:5]=[CH:4][NH:3]1.C(=O)([O-])[O-].[K+].[K+].[F:22][C:23]([F:33])([F:32])[C:24]1[CH:25]=[C:26]([CH:29]=[CH:30][CH:31]=1)[CH2:27]Br>CN(C=O)C>[O:1]=[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:12]([O:14][CH3:15])=[O:13])[CH:10]=2)[N:5]=[CH:4][N:3]1[CH2:27][C:26]1[CH:29]=[CH:30][CH:31]=[C:24]([C:23]([F:22])([F:32])[F:33])[CH:25]=1

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of methyl 4-oxo-3,4-dihydroquinazoline-6-carboxylate (30.6 mg, 0.15 mmol) in DMF (2 mL) was added potassium carbonate (41.5 mg, 0.30 mmol) and 3-(trifluoromethyl)benzyl bromide (45.8 μL, 0.30 mmol). The reaction mixture was heated to 60° C. and stirred overnight. The mixture was then cooled to rt and concentrated. Water was added and the reaction mixture was extracted with DCM (5 mL, 3×). The combined organic phases were then washed with water, and brine, dried over anhydrous Na2SO4, filtered and concentrated to afford methyl 4-oxo-3-[3-(trifluoromethyl)benzyl]-3,4-dihydroquinazoline-6-carboxylate. LC-MS: (FA) ES+ 363.

Workup

temperatureThe mixture was then cooled to rt
concentrationconcentrated
additionWater was added
extractionthe reaction mixture was extracted with DCM (5 mL, 3×)
washThe combined organic phases were then washed with water, and brine
dry with materialdried over anhydrous Na2SO4
filtrationfiltered
concentrationconcentrated

Sources & evidence

ORD record: ord-8683b19c17754c41a7ae62c6ec465536
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08765773B2

Reaction notes

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