Sodium Sulfite → HCID 67260704, compound

HRID 2359041Notes

Reaction equation

HRID 2359041 reaction equation
[Cl:1][C:2]1[S:6][C:5]([C:7]2[C:11]([C:12]3[CH:17]=[CH:16][N:15]=[C:14](SC)[N:13]=3)=[CH:10][N:9]([CH:20]([CH3:22])[CH3:21])[N:8]=2)=[CH:4][CH:3]=1.Cl[C:24]1C=CC=C(C(OO)=O)C=1.[S:34]([O-:37])([O-])=[O:35].[Na+].[Na+]>ClCCl>[Cl:1][C:2]1[S:6][C:5]([C:7]2[C:11]([C:12]3[CH:17]=[CH:16][N:15]=[C:14]([S:34]([CH3:24])(=[O:37])=[O:35])[N:13]=3)=[CH:10][N:9]([CH:20]([CH3:21])[CH3:22])[N:8]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 24437Sodium SulfiteHCID 70297m-Chloroperbenzoic acidHCID 672607724-[3-(5-chloro-2-thienyl)-1-isopropyl-1H-pyrazol-4-yl]-2-(methylsulfanyl)pyrimidine

Product 1

HCID 67260704HCID 67260704, compoundYield 87.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-[3-(5-chloro-2-thienyl)-1-isopropyl-1H-pyrazol-4-yl]-2-(methylsulfanyl)pyrimidine (1 eq, 12 mmol) in 315 mL of dichloromethane was added meta chloroperbenzoic acid 77% (2 eq, 24 mmol). The mixture was stirred at room temperature for 72 h and then quenched with water. Sodium sulfite (2.1 eq, 25 mmol) was added and the layers were separated. The organic layer was then washed twice with a 2M solution of potassium carbonate, dried over MgSO4 filtered and concentrated to afford 4 g of 4-[3-(5-Chloro-2-thienyl)-1-isopropyl-1H-pyrazol-4-yl]-2-(methylsulfonyl)pyrimidine (65% yield) in a 8:2 mixture with the corresponding sulfoxide. The crude material was used in the next step without further purification.

Workup

  1. customquenched with water
  2. customthe layers were separated
  3. washThe organic layer was then washed twice with a 2M solution of potassium carbonate
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-c3b96b74e6f44700bd86629531db6446
Source dataset
uspto-grants-2014_04
Patent number
US08685974B2

Reaction notes

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