Sodium Carbonate → 1-(4-Oxo-5-phenyl-3,4-dihydroquinazolin-2-yl)cyclopropanecarbonitrile

HRID 2036832Notes

Reaction equation

[C:1]([C:3]1([C:6]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[C:10]=2[C:21]([NH2:23])=[O:22])=O)[CH2:5][CH2:4]1)#[N:2].C([O-])([O-])=O.[Na+].[Na+]>CO>[O:22]=[C:21]1[C:10]2[C:9](=[CH:14][CH:13]=[CH:12][C:11]=2[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[N:8]=[C:6]([C:3]2([C:1]#[N:2])[CH2:5][CH2:4]2)[NH:23]1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution 3-(1-cyanocyclopropanecarboxamido)biphenyl-2-carboxamide (0.7 g, 2 mmol) in methanol was added saturated aqueous Na2CO3 (23 mmol) and the reaction mixture stirred at 80° C. for 30 min. The reaction mixture was concentrated under reduced pressure and the resulting residue was diluted with ethyl acetate then washed with water. The organic extracts were dried, concentrated and purified by silica gel chromatography (4% MeOH in DCM) to yield 1-(4-oxo-5-phenyl-3,4-dihydroquinazolin-2-yl)cyclopropanecarbonitrile (0.65 g, 99% yield) as a white solid. LCMS Method T: retention time 1.810 min; [M+1]=288.2.

Workup

concentrationThe reaction mixture was concentrated under reduced pressure
additionthe resulting residue was diluted with ethyl acetate
washthen washed with water
customThe organic extracts were dried
concentrationconcentrated
custompurified by silica gel chromatography (4% MeOH in DCM)

Sources & evidence

ORD record: ord-3a1ff1fd1c9744deb44f16ab95fb6fc6
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08575184B2

Reaction notes

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