Sodium Bicarbonate → 2-(2-chlorobenzyl)-3-(2-methanesulfonyl-pyrimidin-4-yl)-6,7-dihydro-5H-pyrazolo[1,2-a]pyrazol-1-one

HRID 1455244Notes

Reaction equation

HRID 1455244 reaction equation
[Cl:1][C:2]1[CH:25]=[CH:24][CH:23]=[CH:22][C:3]=1[CH2:4][C:5]1[C:12](=[O:13])[N:8]2[CH2:9][CH2:10][CH2:11][N:7]2[C:6]=1[C:14]1[CH:19]=[CH:18][N:17]=[C:16](SC)[N:15]=1.O[O:27][S:28]([O-:30])=O.[K+].S([O-])(O[O-])(=O)=O.[K+].[K+].[C:40]([O-])(O)=O.[Na+]>C1COCC1.CO.O>[Cl:1][C:2]1[CH:25]=[CH:24][CH:23]=[CH:22][C:3]=1[CH2:4][C:5]1[C:12](=[O:13])[N:8]2[CH2:9][CH2:10][CH2:11][N:7]2[C:6]=1[C:14]1[CH:19]=[CH:18][N:17]=[C:16]([S:28]([CH3:40])(=[O:30])=[O:27])[N:15]=1

Participants

7

Reactant 4

HCID 516892Sodium BicarbonateHCID 10313463Potassium peroxymonosulphateHCID 23707502Potassium hydroxy sulfiteHCID 574380712-(2-chlorobenzyl)-3-(2-methylsulfanyl-pyrimidin-4-yl)-6,7-dihydro-5H-pyrazolo[1,2-a]pyrazol-1-one

Product 1

HCID 574380742-(2-chlorobenzyl)-3-(2-methanesulfonyl-pyrimidin-4-yl)-6,7-dihydro-5H-pyrazolo[1,2-a]pyrazol-1-one

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To a cold 0° C. solution of 2-(2-chlorobenzyl)-3-(2-methylsulfanyl-pyrimidin-4-yl)-6,7-dihydro-5H-pyrazolo[1,2-a]pyrazol-1-one, 7, (460 mg, 1.23 mmol)) in THF/MeOH (20 mL of 1:1 mixture) is added dropwise a solution of Oxone® (potassium peroxymonosulfate) (3.0 g, 4.9 mmol) in H2O (15 mL). After stirring the reaction for 1.5 hours at room temperature, the solution is poured into aqueous saturated NaHCO3. The aqueous phase is extracted three times with EtOAc and the combined organic layers are washed with brine, dried (MgSO4), filtered, and concentrated in vacuo to afford 316 mg of the desired product which is used without further purification.

Workup

  1. customthe reaction for 1.5 hours at room temperature
  2. extractionThe aqueous phase is extracted three times with EtOAc
  3. washthe combined organic layers are washed with brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1f2185a3519e49a3944fd90d5a7c7b7b
Source dataset
uspto-grants-2009_01
Patent number
US07482356B2

Reaction notes

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