Acetic Acid → 5-(3,6-dimethyl-2,4-dioxo-1-(3-trifluoromethylphenyl)-1,2,3,4-tetrahydropyrimidin-5-yl-4-(methylsulfonyl)-1H-pyrazol-1-yl)benzonitrile

HRID 576807

Reaction equation

HRID 576807 reaction equation
[CH3:1][N:2]1[C:7](=[O:8])[C:6]([C:9]2[C:13](SC)=[CH:12][N:11]([C:16]3[CH:17]=[CH:18][CH:19]=[C:20]([CH:23]=3)[C:21]#[N:22])[N:10]=2)=[C:5]([CH3:24])[N:4]([C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([C:31]([F:34])([F:33])[F:32])[CH:26]=2)[C:3]1=[O:35].OO.[S:38]([O-:42])([O-])(=[O:40])=S.[Na+].[Na+].[C:45](O)(=O)C>C(OCC)(=O)C.[O-][W]([O-])(=O)=O.[Na+].[Na+]>[CH3:1][N:2]1[C:7](=[O:8])[C:6]([C:9]2[C:13]([S:38]([CH3:45])(=[O:42])=[O:40])=[CH:12][N:11]([C:16]3[CH:17]=[CH:18][CH:19]=[C:20]([CH:23]=3)[C:21]#[N:22])[N:10]=2)=[C:5]([CH3:24])[N:4]([C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([C:31]([F:33])([F:34])[F:32])[CH:26]=2)[C:3]1=[O:35]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 784Hydrogen PeroxideHCID 24477Sodium ThiosulfateHCID 867239105-(3,6-dimethyl-2,4-dioxo-1-(3-trifluoromethylphenyl)-1,2,3,4-tetrahydropyrimidin-5-yl-4-(methylthio)-1H-pyrazol-1-yl)benzonitrile

Product 1

HCID 867239125-(3,6-dimethyl-2,4-dioxo-1-(3-trifluoromethylphenyl)-1,2,3,4-tetrahydropyrimidin-5-yl-4-(methylsulfonyl)-1H-pyrazol-1-yl)benzonitrile

Reagents, catalysts & solvents 2

HCID 26052Sodium tungstateCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-(5-(3,6-dimethyl-2,4-dioxo-1-(3-trifluoromethylphenyl)-1,2,3,4-tetrahydropyrimidin-5-yl-4-(methylthio)-1H-pyrazol-1-yl)benzonitrile (prepared in Example 269) (57.4 mg) in acetic acid (1.0 ml) were added aqueous hydrogen peroxide solution (63.4 μl) and sodium tungstate (3.8 mg) and the resulting mixture was stirred at room temperature for four hours. To the reaction mixture was added 10% aqueous sodium thiosulfate solution (1 ml) and the resulting mixture was stirred at room temperature for one hour. The reaction mixture was diluted with ethyl acetate (50 ml) and then washed with saturated saline (20 ml) and the organic layer was dried over anhydrous sodium sulfate. The organic layer was concentrated under reduced pressure and the residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate) to afford 4-(5-(3,6-dimethyl-2,4-dioxo-1-(3-trifluoromethylphenyl)-1,2,3,4-tetrahydropyrimidin-5-yl-4-(methylsulfonyl)-1H-pyrazol-1-yl)benzonitrile (29.4 mg).

Workup

  1. stirringthe resulting mixture was stirred at room temperature for one hour
  2. washwashed with saturated saline (20 ml)
  3. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  4. concentrationThe organic layer was concentrated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate)

Sources & evidence

ORD record
ord-6856f6251a984124935e6281bfa9d44b
Source dataset
uspto-grants-2015_05
Patent number
US09040516B2

Linked notes

Loading…