(4-(5-(4-chlorophenyl)-4-oxo-1-phenyl-4,5-dihydro-1H-pyrazolo[3,4-d]pyrimidin-6-yl)phenylthio)methyl acetate → (4-(5-(4-chlorophenyl)-4-oxo-1-phenyl-4,5-dihydro-1H-pyrazolo[3,4-d]pyrimidin-6-yl)phenylsulfonyl)methyl acetate

HRID 1024603Notes

Reaction equation

HRID 1024603 reaction equation
[C:1]([O:4][CH2:5][S:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[N:14]([C:29]3[CH:34]=[CH:33][C:32]([Cl:35])=[CH:31][CH:30]=3)[C:15](=[O:28])[C:16]3[CH:21]=[N:20][N:19]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)[C:17]=3[N:18]=2)=[CH:9][CH:8]=1)(=[O:3])[CH3:2].[OH2:36].[OH2:37].O.O.O.O.C1(=O)OOOOC(=O)C2=CC=CC=C12.[Mg]>ClCCl.CO>[C:1]([O:4][CH2:5][S:6]([C:7]1[CH:8]=[CH:9][C:10]([C:13]2[N:14]([C:29]3[CH:30]=[CH:31][C:32]([Cl:35])=[CH:33][CH:34]=3)[C:15](=[O:28])[C:16]3[CH:21]=[N:20][N:19]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)[C:17]=3[N:18]=2)=[CH:11][CH:12]=1)(=[O:37])=[O:36])(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 57899441(4-(5-(4-chlorophenyl)-4-oxo-1-phenyl-4,5-dihydro-1H-pyrazolo[3,4-d]pyrimidin-6-yl)phenylthio)methyl acetateHCID 86596527CID 86596527

Product 1

HCID 57899401(4-(5-(4-chlorophenyl)-4-oxo-1-phenyl-4,5-dihydro-1H-pyrazolo[3,4-d]pyrimidin-6-yl)phenylsulfonyl)methyl acetate

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of (4-(5-(4-chlorophenyl)-4-oxo-1-phenyl-4,5-dihydro-1H-pyrazolo[3,4-d]pyrimidin-6-yl)phenylthio)methyl acetate (1.00 g, 1.98 mmol) in dry dichloromethane (30 mL) and methanol (10 mL), magnesium monoperoxy phthalate hexahydrate (1.08 g, 2.18 mmol) is added at 0° C. and the resulting mixture is stirred for 18 h at rt. Then 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 (4-(5-(4-chlorophenyl)-4-oxo-1-phenyl-4,5-dihydro-1H-pyrazolo[3,4-d]pyrimidin-6-yl)phenylsulfonyl)methyl acetate.

Workup

  1. customThen the 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-2c13f27e353a459e92f00d662fb3a91d
Source dataset
uspto-grants-2014_05
Patent number
US08722691B2

Reaction notes

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