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

HRID 1061602Notes

Reaction equation

HRID 1061602 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:15](=[O:16])[N:11]3[CH2:12][CH2:13][CH2:14][N:10]3[C:9]=2[C:17]2[CH:22]=[CH:21][N:20]=[C:19](SC)[N:18]=2)=[CH:4][CH:3]=1.[CH3:25]O.O[O:28][S:29]([O-:31])=O.[K+].S([O-])(O[O-])(=O)=O.[K+].[K+]>C1COCC1.O.C([O-])(O)=O.[Na+]>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:15](=[O:16])[N:11]3[CH2:12][CH2:13][CH2:14][N:10]3[C:9]=2[C:17]2[CH:22]=[CH:21][N:20]=[C:19]([S:29]([CH3:25])(=[O:31])=[O:28])[N:18]=2)=[CH:4][CH:3]=1

Participants

8

Reactant 4

HCID 887MethanolHCID 10313463Potassium peroxymonosulphateHCID 129914042-(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 129914052-(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 2-(4-fluorophenyl)-3-(2-methylsulfanyl-pyrimidin-4-yl)-6,7-dihydro-5H-pyrazolo[1,2-a]pyrazol-1-one, 4, (1.3 g, 3.8 mmol) in THF:methanol (56 mL of a 1:1 mixture) is added dropwise a solution of Oxone® (potassium peroxymonosulfate) (9.34 g, 15.2 mmol) in water (42 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 too 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-19bb04a4529249adac378964ba3683a3
Source dataset
uspto-grants-2005_11
Patent number
US06960593B2

Reaction notes

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