Methanol → 2-(Methylsulfonyl)-4-[4-(trifluoromethyl)phenyl]pyrimidine

HRID 1269625Notes

Reaction equation

HRID 1269625 reaction equation
CS[C:3]1[N:8]=[C:7]([C:9]2[CH:14]=[CH:13][C:12]([C:15]([F:18])([F:17])[F:16])=[CH:11][CH:10]=2)[CH:6]=[CH:5][N:4]=1.O[O:20][S:21]([O-:23])=O.[K+].[CH3:25]O>O>[CH3:25][S:21]([C:3]1[N:8]=[C:7]([C:9]2[CH:10]=[CH:11][C:12]([C:15]([F:18])([F:16])[F:17])=[CH:13][CH:14]=2)[CH:6]=[CH:5][N:4]=1)(=[O:23])=[O:20]

Participants

5

Reactant 3

HCID 887MethanolHCID 184483552-Methylsulfanyl-4-(4-trifluoromethylphenyl)pyrimidineHCID 23707502Potassium hydroxy sulfite

Product 1

HCID 184483542-(Methylsulfonyl)-4-[4-(trifluoromethyl)phenyl]pyrimidine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
0 °C

Procedure

To a suspension of 2-(methylthio)-4-[4-(trifluoromethyl)phenyl]pyrimidine (2.24 g, 8.4 mmol) in methanol (85 mL) and water (85 mL) at 0° C. was added oxone™ (15.25 g, 24.8 mmol). The reaction was stirred at 0° C. for 1 h and then at room temperature for 18 h. The reaction mixture was diluted with water (200 mL) and extracted with chloroform (2×250 mL). The organic solution was dried (Na2SO4) filtered and evaporated to afford the title compound as a white solid (2.235 g).

Workup

  1. waitat room temperature for 18 h
  2. extractionextracted with chloroform (2×250 mL)
  3. dry with materialThe organic solution was dried (Na2SO4)
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-59ca30d8c1cc4c139472372c9ce1e541
Source dataset
uspto-grants-2007_04
Patent number
US07199239B2

Reaction notes

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