Acetic Acid → 5-methyl-3-(methylsulfinyl)-2-(4-(methylsulfonyl)benzyl)-7-neopentyl-2H-pyrazolo[3,4-d]pyrimidine-4,6(5H,7H)-dione

HRID 535893Notes

Reaction equation

HRID 535893 reaction equation
[CH3:1][N:2]1[C:7](=[O:8])[C:6]2=[C:9]([S:23][CH3:24])[N:10]([CH2:12][C:13]3[CH:18]=[CH:17][C:16]([S:19]([CH3:22])(=[O:21])=[O:20])=[CH:15][CH:14]=3)[N:11]=[C:5]2[N:4]([CH2:25][C:26]([CH3:29])([CH3:28])[CH3:27])[C:3]1=[O:30].OO.C(O)(=[O:35])C>C(Cl)Cl.CC#N>[CH3:1][N:2]1[C:7](=[O:8])[C:6]2=[C:9]([S:23]([CH3:24])=[O:35])[N:10]([CH2:12][C:13]3[CH:14]=[CH:15][C:16]([S:19]([CH3:22])(=[O:20])=[O:21])=[CH:17][CH:18]=3)[N:11]=[C:5]2[N:4]([CH2:25][C:26]([CH3:27])([CH3:29])[CH3:28])[C:3]1=[O:30]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 784Hydrogen PeroxideHCID 462206415-methyl-2-(4-(methylsulfonyl)benzyl)-3-(methylthio)-7-neopentyl-2H-pyrazolo[3,4-d]pyrimidine-4,6(5H,7H)-dione

Product 1

HCID 462206425-methyl-3-(methylsulfinyl)-2-(4-(methylsulfonyl)benzyl)-7-neopentyl-2H-pyrazolo[3,4-d]pyrimidine-4,6(5H,7H)-dioneYield 58.5%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

5-methyl-2-(4-(methylsulfonyl)benzyl)-3-(methylthio)-7-neopentyl-2H-pyrazolo[3,4-d]pyrimidine-4,6(5H,7H)-dione (11.4 mg, 0.022 mmol) is dissolved in CH2Cl2 (200 μL) and CH3CN (100 μL), and then 30% H2O2 aqueous solution (75 μL, 0.66 mmol) is added, followed by acetic acid (6.6 mg, 0.11 mmol). The reaction mixture is stirred at room temperature over a weekend, and then purified by a semi-preparative HPLC to give 6 mg of product as white solids. MS (ESI) m/z 467.1 [M+H]+.

Workup

  1. custompurified by a semi-preparative HPLC

Sources & evidence

ORD record
ord-50074f7ce93d4eb1aae6c89df459d7d7
Source dataset
uspto-grants-2014_10
Patent number
US08859564B2

Reaction notes

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