Water → 4'-[(4-Butyl-2-methyl-6-oxo-1,6-dihydropyrimidin-5-yl)methyl]-3'-fluorobiphenyl-2-carbonitrile
Reaction equation
Cl.[C:2]([NH2:5])(=[NH:4])[CH3:3].C[O-].[Na+].[C:9]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[C:17]1[CH:22]=[CH:21][C:20]([CH2:23][CH:24]([C:29](=O)[CH2:30][CH2:31][CH2:32][CH3:33])[C:25](OC)=[O:26])=[C:19]([F:35])[CH:18]=1)#[N:10].O>CO>[CH2:30]([C:29]1[N:4]=[C:2]([CH3:3])[NH:5][C:25](=[O:26])[C:24]=1[CH2:23][C:20]1[CH:21]=[CH:22][C:17]([C:12]2[C:11]([C:9]#[N:10])=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:18][C:19]=1[F:35])[CH2:31][CH2:32][CH3:33]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
To a suspension of acetamidine hydrochloride (6.7 g) in methanol (50 mL) were added sodium methoxide (28% methanol solution, 20.5 mL) and then methyl 2-[(2′-cyano-3-fluorobiphenyl-4-yl)methyl]-3-oxoheptanoate (13.0 g), and the mixture was stirred for 15 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate, and the solvent was evaporated. The residue was triturated with diisopropyl ether to give the title compound (9.15 g, 69%) as pale-yellow crystals.
Workup
- extractionthe mixture was extracted with ethyl acetate
- washThe organic layer was washed with saturated brine
- dry with materialdried over anhydrous magnesium sulfate
- customthe solvent was evaporated
- customThe residue was triturated with diisopropyl ether
Sources & evidence
- ORD record
- ord-b65dfd68804147ecbbba6bedc12ad59f
- Source dataset
- uspto-grants-2011_08
- Patent number
- US07998968B2
Reaction notes
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