Water → 4'-[(4-Butyl-2-methyl-6-oxo-1,6-dihydropyrimidin-5-yl)methyl]-3',5'-difluorobiphenyl-2-carbonitrile

HRID 1718641Notes

Reaction equation

HRID 1718641 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]=[C:21]([F:23])[C:20]([CH2:24][CH:25]([C:30](=O)[CH2:31][CH2:32][CH2:33][CH3:34])[C:26](OC)=[O:27])=[C:19]([F:36])[CH:18]=1)#[N:10].O>CO>[CH2:31]([C:30]1[N:4]=[C:2]([CH3:3])[NH:5][C:26](=[O:27])[C:25]=1[CH2:24][C:20]1[C:21]([F:23])=[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:36])[CH2:32][CH2:33][CH3:34]

Participants

6

Reactant 4

HCID 962WaterHCID 67170Acetamidine monohydrochlorideHCID 10942334Sodium MethoxideHCID 57460540Methyl 2-[(2'-cyano-3,5-difluorobiphenyl-4-yl)methyl]-3-oxoheptanoate

Product 1

HCID 1361468224'-[(4-Butyl-2-methyl-6-oxo-1,6-dihydropyrimidin-5-yl)methyl]-3',5'-difluorobiphenyl-2-carbonitrileYield 63.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a suspension of acetamidine hydrochloride (3.9 g) in methanol (30 mL) were added sodium methoxide (28% methanol solution, 12 mL) and then methyl 2-[(2′-cyano-3,5-difluorobiphenyl-4-yl)methyl]-3-oxoheptanoate (7.93 g), and the mixture was stirred for 15 hr. Water was added to the reaction mixture, and the aqueous layer 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 (5.11 g, 63%) as pale-yellow crystals.

Workup

  1. extractionthe aqueous layer was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated
  5. customThe residue was triturated with diisopropyl ether

Sources & evidence

ORD record
ord-db8b0671bf7a4f30967b033e4bf712b3
Source dataset
uspto-grants-2010_09
Patent number
US07803940B2

Reaction notes

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