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

HRID 1455241Notes

Reaction equation

HRID 1455241 reaction equation
CS[C:3]1[N:8]=[C:7]([C:9]2[N:13]3[CH2:14][CH2:15][CH2:16][N:12]3[C:11](=[O:17])[C:10]=2[O:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[CH3:25])[CH:6]=[CH:5][N:4]=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.O.CO>[CH3:40][S:28]([C:3]1[N:8]=[C:7]([C:9]2[N:13]3[CH2:14][CH2:15][CH2:16][N:12]3[C:11](=[O:17])[C:10]=2[O:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[CH3:25])[CH:6]=[CH:5][N:4]=1)(=[O:30])=[O:27]

Participants

8

Reactant 4

HCID 516892Sodium BicarbonateHCID 10313463Potassium peroxymonosulphateHCID 23707502Potassium hydroxy sulfiteHCID 574380663-(2-methylsulfanyl-pyrimidin-4-yl)-2-o-tolyloxy-6,7-dihydro-5H-pyrazolo[1,2-a]pyrazol-1-one

Product 1

HCID 575317883-(2-Methanesulfonyl-pyrimidin-4-yl)-2-o-tolyloxy-6,7-dihydro-5H-pyrazolo[1,2-a]pyrazol-1-one

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-(2-methylsulfanyl-pyrimidin-4-yl)-2-o-tolyloxy-6,7-dihydro-5H-pyrazolo[1,2-a]pyrazol-1-one, 2, (0.20 g, 0.56 mmol) in THF:methanol (6 mL of 1:1 mixture) is added dropwise a solution of Oxone® (potassium peroxymonosulfate) (1.37 g, 2.24 mmol) in H2O (6 mL). After stirring the reaction for 1 hour at room temperature, the solution is poured into aqueous saturated NaHCO3. The aqueous phase is extracted three times with EtOAc, the organic phases are combined, dried (MgSO4), filtered and concentrated in vacuo to afford the desired product which is used without further purification.

Workup

  1. customthe reaction for 1 hour at room temperature
  2. extractionThe aqueous phase is extracted three times with EtOAc
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-dbd857b016c54a3fb7ba16bd789e21f8
Source dataset
uspto-grants-2009_01
Patent number
US07482356B2

Reaction notes

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