Water → 2-(methylsulfonyl)-4-(1-phenyl-1H-pyrazol-5-yl)pyrimidine

HRID 2214777Notes

Reaction equation

HRID 2214777 reaction equation
[OH:1]OS([O-])=O.[K+].[CH3:7][S:8][C:9]1[N:14]=[C:13]([C:15]2[N:19]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[N:18]=[CH:17][CH:16]=2)[CH:12]=[CH:11][N:10]=1.[OH2:26]>CO>[CH3:7][S:8]([C:9]1[N:14]=[C:13]([C:15]2[N:19]([C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)[N:18]=[CH:17][CH:16]=2)[CH:12]=[CH:11][N:10]=1)(=[O:1])=[O:26]

Participants

5

Reactant 3

HCID 962WaterHCID 219485112-(methylthio)-4-(1-phenyl-1H-pyrazol-5-yl)pyrimidineHCID 23707502Potassium hydroxy sulfite

Product 1

HCID 219484652-(methylsulfonyl)-4-(1-phenyl-1H-pyrazol-5-yl)pyrimidine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of oxone (521 mg, 0.850 mmol, 1.30 equiv) in water (10 mL) was added to a solution of 2-(methylthio)-4-(1-phenyl-1H-pyrazol-5-yl)pyrimidine (1-5, 175 mg, 0.652 mmol, 1 equiv) in methanol (20 mL) at 23° C., and the resulting mixture was stirred for 20 hours. The reaction mixture was partitioned between brine and ethyl acetate (3×75 mL). The combined organic layers were dried over sodium sulfate and concentrated to give 2-(methylsulfonyl)-4-(1-phenyl-1H-pyrazol-5-yl)pyrimidine (1-7) as a white solid.

Workup

  1. customThe reaction mixture was partitioned between brine and ethyl acetate (3×75 mL)
  2. dry with materialThe combined organic layers were dried over sodium sulfate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-ff38e3f19fcb4a1d9a3b44e273c9ed02
Source dataset
uspto-grants-2006_09
Patent number
US07109204B2

Reaction notes

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