5-(4-Chloro-phenyl)-6-(4-methylsulfanyl-phenyl)-1-phenyl-1,5-dihydro-pyrazolo[3,4-d]pyrimidin-4-one → 5-(4-Chloro-phenyl)-6-(4-methanesulfinyl-phenyl)-1-phenyl-1,5-dihydro-pyrazolo[3,4-d]pyrimidin-4-one

HRID 1024601Notes

Reaction equation

HRID 1024601 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:13](=[O:14])[C:12]3[CH:15]=[N:16][N:17]([C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)[C:11]=3[N:10]=[C:9]2[C:24]2[CH:29]=[CH:28][C:27]([S:30][CH3:31])=[CH:26][CH:25]=2)=[CH:4][CH:3]=1.O.O.O.O.O.O.C1(=O)OOOOC(=[O:42])C2=CC=CC=C12.[Mg]>ClCCl.CO>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[C:13](=[O:14])[C:12]3[CH:15]=[N:16][N:17]([C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)[C:11]=3[N:10]=[C:9]2[C:24]2[CH:25]=[CH:26][C:27]([S:30]([CH3:31])=[O:42])=[CH:28][CH:29]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 578993915-(4-Chloro-phenyl)-6-(4-methylsulfanyl-phenyl)-1-phenyl-1,5-dihydro-pyrazolo[3,4-d]pyrimidin-4-oneHCID 86596527CID 86596527

Product 1

HCID 578993935-(4-Chloro-phenyl)-6-(4-methanesulfinyl-phenyl)-1-phenyl-1,5-dihydro-pyrazolo[3,4-d]pyrimidin-4-one

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-(4-chloro-phenyl)-6-(4-methylsulfanyl-phenyl)-1-phenyl-1,5-dihydro-pyrazolo[3,4-d]pyrimidin-4-one (2.10 g, 4.72 mmol) in dry dichloromethane (36 mL) and methanol (12 mL), magnesium monoperoxy phthalate hexahydrate (1.16 g, 2.36 mmol) is added at 0° C. and the resulting mixture is stirred for 3 h at that temperature. The reaction mixture is quenched with the addition of 10% sodium bicarbonate solution and extracted with dichloromethane (3×). The organic part separated is dried (Na2SO4) and concentrated. The crude product is purified by column chromatography (silica gel, 60-120 mesh) to afford 5-(4-chloro-phenyl)-6-(4-methanesulfinyl-phenyl)-1-phenyl-1,5-dihydro-pyrazolo[3,4-d]pyrimidin-4-one.

Workup

  1. customThe reaction mixture is quenched with the addition of 10% sodium bicarbonate solution
  2. extractionextracted with dichloromethane (3×)
  3. customThe organic part separated
  4. dry with materialis dried (Na2SO4)
  5. concentrationconcentrated
  6. customThe crude product is purified by column chromatography (silica gel, 60-120 mesh)

Sources & evidence

ORD record
ord-78b9d8d24aef44829413b96227ddee03
Source dataset
uspto-grants-2014_05
Patent number
US08722691B2

Reaction notes

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