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

HRID 1581516Notes

Reaction equation

HRID 1581516 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-6dc20d508eaf4cfa95c4a9a74b167c68
Source dataset
uspto-grants-2004_05
Patent number
US06730668B2

Reaction notes

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