Water → HCID 21948461, compound

HRID 2214784Notes

Reaction equation

HRID 2214784 reaction equation
[OH:1]OS([O-])=O.[K+].[CH3:7][S:8][C:9]1[N:14]=[C:13]([C:15]2[NH:19][N:18]=[CH:17][C:16]=2[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=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[NH:19][N:18]=[CH:17][C:16]=2[C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH:12]=[CH:11][N:10]=1)=[O:1].[CH3:7][S:8]([C:9]1[N:14]=[C:13]([C:15]2[NH:19][N:18]=[CH:17][C:16]=2[C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH:12]=[CH:11][N:10]=1)(=[O:1])=[O:26]

Participants

6

Reactant 3

HCID 962WaterHCID 21948510HCID 21948510, compoundHCID 23707502Potassium hydroxy sulfite

Product 2

HCID 21948461HCID 21948461, compoundHCID 21948509HCID 21948509, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of Oxone (538 mg, 0.88 mmol, 1.2 equiv) in water (3 mL) was added to a solution of 2-(methylthio)-4-(4-phenyl-1H-pyrazol-5-yl)pyrimidine (3-3, 196 mg, 0.73 mmol, 1 equiv) in methanol (50 mL), and the resulting mixture was stirred under ambient conditions for 18 hours. The reaction was concentrated and the residue was partitioned between ethyl acetate and saturated sodium bicarbonate solution. The organic layer was washed with brine, dried over magnesium sulfate and concentrated to give a mixture (3:2) of 2-(methylsulfinyl)-4-(4-phenyl-1H-pyrazol-5-yl)pyrimidine (3-4) and 2-(methylsulfonyl)-4-(4-phenyl-1H-pyrazol-5-yl)pyrimidine (3-5), respectively.

Workup

  1. concentrationThe reaction was concentrated
  2. customthe residue was partitioned between ethyl acetate and saturated sodium bicarbonate solution
  3. washThe organic layer was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-724006bf3f1f48c9bf0536455bca353d
Source dataset
uspto-grants-2006_09
Patent number
US07109204B2

Reaction notes

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