Sodium Bicarbonate → HCID 69218330, compound

HRID 2251088Notes

Reaction equation

HRID 2251088 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]([C:10]1[N:20]([C:21]2[N:22]([CH3:27])[N:23]=[C:24]([CH3:26])[CH:25]=2)[C:13]2[N:14]=[C:15](SC)[N:16]=[CH:17][C:12]=2[CH:11]=1)=[O:9].O[O:29][S:30]([O-:32])=O.[K+].S([O-])(O[O-])(=O)=O.[K+].[K+].[C:42]([O-])(O)=O.[Na+]>C1COCC1.O.CO>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]([C:10]1[N:20]([C:21]2[N:22]([CH3:27])[N:23]=[C:24]([CH3:26])[CH:25]=2)[C:13]2[N:14]=[C:15]([S:30]([CH3:42])(=[O:32])=[O:29])[N:16]=[CH:17][C:12]=2[CH:11]=1)=[O:9]

Participants

8

Reactant 4

HCID 516892Sodium BicarbonateHCID 10313463Potassium peroxymonosulphateHCID 23707502Potassium hydroxy sulfiteHCID 59643068HCID 59643068, compound

Product 1

HCID 69218330HCID 69218330, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (2-chloro-phenyl)-[7-(2,5-dimethyl-2H-pyrazol-3-yl)-2-methylsulfanyl-7H-pyrrolo[2,3-d]pyrimidin-6-yl]-methanone, 19, (0.13 g, 0.34 mmol) in THF:methanol (4 mL of 1:1 mixture) is added dropwise a solution of Oxone® (potassium peroxymonosulfate) (0.73 g, 1.19 mmol) in H2O (4 mL). After stirring the reaction for 1 hour at room temperature, the solution is poured into aqueous saturated NaHCO3. The aqueous phase is twice extracted with CHCl3 and the combined organic phases are dried (MgSO4), filtered and concentrated in vacuo to afford 0.12 g of the desired product which is used without further purification.

Workup

  1. customthe reaction for 1 hour at room temperature
  2. extractionThe aqueous phase is twice extracted with CHCl3
  3. dry with materialthe combined organic phases are dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d74f5962af424888a8e8be64dd967a1e
Source dataset
uspto-grants-2008_01
Patent number
US07319102B1

Reaction notes

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