Hydrogen Peroxide → 5-(2-Methylsulfonylpyrimidin-4-yl)-6-(3-trifluoromethylphenyl)-4,5-dihydro-2H-pyridazin-3-one

HRID 394475

Reaction equation

HRID 394475 reaction equation
CS[C:3]1[N:8]=[C:7]([CH:9]2[C:14]([C:15]3[CH:20]=[CH:19][CH:18]=[C:17]([C:21]([F:24])([F:23])[F:22])[CH:16]=3)=[N:13][NH:12][C:11](=[O:25])[CH2:10]2)[CH:6]=[CH:5][N:4]=1.OO.[CH3:28]O.[S:30](S([O-])=O)([O-:32])=[O:31].[Na+].[Na+]>[O-][W]([O-])(=O)=O.[Na+].[Na+].C(OCC)(=O)C>[CH3:28][S:30]([C:3]1[N:8]=[C:7]([CH:9]2[C:14]([C:15]3[CH:20]=[CH:19][CH:18]=[C:17]([C:21]([F:24])([F:23])[F:22])[CH:16]=3)=[N:13][NH:12][C:11](=[O:25])[CH2:10]2)[CH:6]=[CH:5][N:4]=1)(=[O:32])=[O:31]

Participants

7

Reactant 4

HCID 784Hydrogen PeroxideHCID 887MethanolHCID 24489Sodium DithioniteHCID 181766265-(2-Methylsulfanylpyrimidin-4-yl)-6-(3-trifluoromethylphenyl)-4,5-dihydro-2H-pyridazin-3-one

Product 1

HCID 181766135-(2-Methylsulfonylpyrimidin-4-yl)-6-(3-trifluoromethylphenyl)-4,5-dihydro-2H-pyridazin-3-one

Reagents, catalysts & solvents 2

HCID 26052Sodium tungstateCatalystHCID 8857Ethyl AcetateSolvent

Procedure

Compound 6 (17.8 mmol), sodium tungstate (587 mg, 1.78 mmol), 30% hydrogen peroxide (8.07 mL, 71.2 mmol), methanol (20 mL), and ethyl acetate (200 mL) were combined under argon, then heated to reflux for 4 h. The solution was cooled and aqueous sodium hydrosulfite was added. The methanol was removed in vacuo and saturated sodium bicarbonate was added. The resulting suspension was extracted several times with methylene chloride. The combined organic extracts were washed successively with water and brine. The organic layer was dried with anhydrous sodium sulfate then concentrated in vacuo to give Compound 7 as a foam: 5.0 g (13 mmol, 73% (two steps))

Workup

  1. temperatureheated
  2. temperatureto reflux for 4 h
  3. temperatureThe solution was cooled
  4. customThe methanol was removed in vacuo and saturated sodium bicarbonate
  5. additionwas added
  6. extractionThe resulting suspension was extracted several times with methylene chloride
  7. washThe combined organic extracts were washed successively with water and brine
  8. dry with materialThe organic layer was dried with anhydrous sodium sulfate
  9. concentrationthen concentrated in vacuo

Sources & evidence

ORD record
ord-c0547385b9c942c6ba5de8f00893f129
Source dataset
uspto-grants-2003_08
Patent number
US06602872B1

Linked notes

Loading…