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

HRID 22678

Reaction equation

HRID 22678 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-a86e3a986d9d48189cb721c80156fa5b
Source dataset
uspto-grants-2005_02
Patent number
US06849627B2

Linked notes

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