Water → 1-(4-cyanophenyl)-5-(3,6-dimethyl-2,4-dioxo-1-(3-trifluoromethylphenyl)-1,2,3,4-tetrahydropyrimidin-5-yl)-1H-pyrazole-4-sulfonic acid

HRID 576796Notes

Reaction equation

HRID 576796 reaction equation
[CH3:1][N:2]1[C:7](=[O:8])[C:6]([C:9]2[N:13]([C:14]3[CH:21]=[CH:20][C:17]([C:18]#[N:19])=[CH:16][CH:15]=3)[N:12]=[CH:11][CH:10]=2)=[C:5]([CH3:22])[N:4]([C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([C:29]([F:32])([F:31])[F:30])[CH:24]=2)[C:3]1=[O:33].[S:34](=O)(=[O:37])([OH:36])[OH:35].O.C(OCC)(=O)C>C(#N)C>[C:18]([C:17]1[CH:16]=[CH:15][C:14]([N:13]2[C:9]([C:6]3[C:7](=[O:8])[N:2]([CH3:1])[C:3](=[O:33])[N:4]([C:23]4[CH:28]=[CH:27][CH:26]=[C:25]([C:29]([F:30])([F:31])[F:32])[CH:24]=4)[C:5]=3[CH3:22])=[C:10]([S:34]([OH:37])(=[O:36])=[O:35])[CH:11]=[N:12]2)=[CH:21][CH:20]=1)#[N:19]

Participants

6

Reactant 4

HCID 962WaterHCID 1118Sulfuric AcidHCID 8857Ethyl AcetateHCID 712514174-[5-[3,6-dimethyl-2,4-dioxo-1-(3-trifluoromethylphenyl)-1,2,3,4-tetrahydropyrimidin-5-yl]-1H-pyrazol-1-yl]benzonitrile

Product 1

HCID 715138621-(4-cyanophenyl)-5-(3,6-dimethyl-2,4-dioxo-1-(3-trifluoromethylphenyl)-1,2,3,4-tetrahydropyrimidin-5-yl)-1H-pyrazole-4-sulfonic acid

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a suspension of the compound prepared in Example 1 (2.0 g) in acetonitrile (20 ml) was added concentrated sulfuric acid (1.08 ml) and the resulting mixture was stirred with heating under reflux for three hours. The reaction mixture was cooled to room temperature and thereto were added water (40 ml) and ethyl acetate (40 ml×1, 20 ml×1) such that the intended products were extracted into an organic layer. The organic layer was washed with saturated saline (20 ml), dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. To the residue was added chloroform (10 ml) and the resulting mixture was stirred at 60° C. for thirty minutes. The mixture was stirred at room temperature overnight and the precipitated crystals were collected by filtration and washed with chloroform to afford 1-(4-cyanophenyl)-5-(3,6-dimethyl-2,4-dioxo-1-(3-trifluoromethylphenyl)-1,2,3,4-tetrahydropyrimidin-5-yl)-1H-pyrazole-4-sulfonic acid (2.06 g).

Workup

  1. temperaturewith heating
  2. temperatureunder reflux for three hours
  3. extractionwere extracted into an organic layer
  4. washThe organic layer was washed with saturated saline (20 ml)
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. additionTo the residue was added chloroform (10 ml)
  8. stirringthe resulting mixture was stirred at 60° C. for thirty minutes
  9. stirringThe mixture was stirred at room temperature overnight
  10. filtrationthe precipitated crystals were collected by filtration
  11. washwashed with chloroform

Sources & evidence

ORD record
ord-7b1e907223d942b89260d1882a427026
Source dataset
uspto-grants-2015_05
Patent number
US09040516B2

Reaction notes

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