Methanol → 6-dimethylamino-2-(4-fluorophenyl)-3-(2-methanesulfonyl-pyrimidin-4-yl)-6,7-dihydro-5H-pyrazolo[1,2-a]pyrazol-1-one

HRID 2220939Notes

Reaction equation

HRID 2220939 reaction equation
[CH3:1][N:2]([CH3:27])[CH:3]1[CH2:7][N:6]2[C:8](=[O:26])[C:9]([C:19]3[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=3)=[C:10]([C:11]3[CH:16]=[CH:15][N:14]=[C:13](SC)[N:12]=3)[N:5]2[CH2:4]1.[CH3:28]O.O[O:31][S:32]([O-:34])=O.[K+].S([O-])(O[O-])(=O)=O.[K+].[K+]>C1COCC1.O.C([O-])(O)=O.[Na+]>[CH3:27][N:2]([CH3:1])[CH:3]1[CH2:7][N:6]2[C:8](=[O:26])[C:9]([C:19]3[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=3)=[C:10]([C:11]3[CH:16]=[CH:15][N:14]=[C:13]([S:32]([CH3:28])(=[O:34])=[O:31])[N:12]=3)[N:5]2[CH2:4]1

Participants

8

Reactant 4

HCID 887MethanolHCID 10313463Potassium peroxymonosulphateHCID 219922076-dimethylamino-2-(4-fluorophenyl)-3-(2-methylsulfanyl-pyrimidin-4-yl)-6,7-dihydro-5H-pyrazolo[1,2-a]pyrazol-1-oneHCID 23707502Potassium hydroxy sulfite

Product 1

HCID 219922086-dimethylamino-2-(4-fluorophenyl)-3-(2-methanesulfonyl-pyrimidin-4-yl)-6,7-dihydro-5H-pyrazolo[1,2-a]pyrazol-1-one

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a solution of 6-dimethylamino-2-(4-fluorophenyl)-3-(2-methylsulfanyl-pyrimidin-4-yl)-6,7-dihydro-5H-pyrazolo[1,2-a]pyrazol-1-one, 24, (3.9 g, 10 mmol) in THF:methanol (150 mL of a 1:1 mixture) is added dropwise a solution of Oxone® (potassium peroxymonosulfate) (24.3 g, 39.5 mmol) in water (100 mL). The reaction is stirred 1 hour at room temperature, diluted with aqueous NaHCO3 and extract three times with ethyl acetate. The organic layers are combined, dried, and concentrated in vacuo to afford the crude desired product which is used without further purification.

Workup

  1. extractionextract three times with ethyl acetate
  2. customdried
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-62f3b07dfd5949d68efdafd68afbd58f
Source dataset
uspto-grants-2008_05
Patent number
US07368455B2

Reaction notes

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