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

HRID 1455261Notes

Reaction equation

HRID 1455261 reaction equation
[Cl:1][C:2]1[CH:26]=[CH:25][CH:24]=[CH:23][C:3]=1[C:4]([C:6]1[C:13](=[O:14])[N:9]2[CH2:10][CH2:11][CH2:12][N:8]2[C:7]=1[C:15]1[CH:20]=[CH:19][N:18]=[C:17](SC)[N:16]=1)=[O:5].O[O:28][S:29]([O-:31])=O.[K+].S([O-])(O[O-])(=O)=O.[K+].[K+].[C:41]([O-])(O)=O.[Na+]>C1COCC1.CO.O>[Cl:1][C:2]1[CH:26]=[CH:25][CH:24]=[CH:23][C:3]=1[C:4]([C:6]1[C:13](=[O:14])[N:9]2[CH2:10][CH2:11][CH2:12][N:8]2[C:7]=1[C:15]1[CH:20]=[CH:19][N:18]=[C:17]([S:29]([CH3:41])(=[O:31])=[O:28])[N:16]=1)=[O:5]

Participants

7

Reactant 4

HCID 516892Sodium BicarbonateHCID 10313463Potassium peroxymonosulphateHCID 23707502Potassium hydroxy sulfiteHCID 574381002-(2-chlorobenzoyl)-3-(2-methylsulfanyl-pyrimidin-4-yl)-6,7-dihydro-5H-pyrazolo[1,2-a]pyrazol-1-one

Product 1

HCID 574381012-(2-chlorobenzoyl)-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 solution of 2-(2-chloro-benzoyl)-3-(2-methylsulfanyl-pyrimidin-4-yl)-6,7-dihydro-5H-pyrazolo[1,2-a]pyrazol-1-one, 23, (0.15 g, 0.39 mmol)) in THF/MeOH (3 mL of 1:1 mixture) is added dropwise a solution of Oxone® (potassium peroxymonosulfate) (0.72 g, 1.16 mmol) in H2O (3 mL). After stirring the reaction for 1.5 hour at room temperature, the solution is poured into aqueous saturated NaHCO3. The aqueous phase is extracted three times with CHCl3 and the combined organic phases are dried (MgSO4), filtered and concentrated in vacuo. The crude product is used without further purification.

Workup

  1. customthe reaction for 1.5 hour at room temperature
  2. extractionThe aqueous phase is extracted three times with CHCl3
  3. dry with materialthe combined organic phases are dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude product is used without further purification

Sources & evidence

ORD record
ord-da8bd7edde8b48ecb60893e5a9ee192f
Source dataset
uspto-grants-2009_01
Patent number
US07482356B2

Reaction notes

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