Hydrogen Peroxide → HCID 25055469, compound

HRID 1513035Notes

Reaction equation

HRID 1513035 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[C:5]([O:10][CH2:11][C:12]2[C:17]([O:18][CH3:19])=[CH:16][CH:15]=[C:14]([F:20])[C:13]=2[F:21])=[CH:4][C:3]=1[N:22]1[C:30](=[O:31])[NH:29][C:28]2[C:23]1=[N:24][C:25]([C:32]#[N:33])=[N:26][CH:27]=2.[OH-].[Na+].OO.S([O-])([O-])=[O:39].[Na+].[Na+]>CS(C)=O>[C:32]([C:25]1[N:24]=[C:23]2[C:28]([NH:29][C:30](=[O:31])[N:22]2[C:3]2[CH:4]=[C:5]([O:10][CH2:11][C:12]3[C:17]([O:18][CH3:19])=[CH:16][CH:15]=[C:14]([F:20])[C:13]=3[F:21])[C:6]([O:8][CH3:9])=[CH:7][C:2]=2[Cl:1])=[CH:27][N:26]=1)(=[O:39])[NH2:33]

Participants

6

Reactant 4

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 24437Sodium SulfiteHCID 25055468HCID 25055468, compound

Product 1

HCID 25055469HCID 25055469, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of 9-[2-chloro-5-(2,3-difluoro-6-methoxybenzyloxy)-4-methoxyphenyl]-2-cyano-7,9-dihydro-8H-purin-8-one (43 mg) in dimethyl sulfoxide (2 mL) were added 2 mol/L aqueous sodium hydroxide solution (0.14 mL) and 30% aqueous hydrogen peroxide solution (0.02 mL), and the mixture was stirred at room temperature for 1 hour. To the reaction mixture was added 10% aqueous sodium sulfite solution, and the resulting mixture was stirred at room temperature for 10 minutes, and extracted with ethyl acetate. The extract was washed with water and brine, and dried over anhydrous sodium sulfate, and the solvent was removed under reduced pressure. The residual solids were suspended in a mixed solvent (n-hexane/ethyl acetate=1/1), and collected by filtration. The collected solids were washed with the same solvent, and dried under reduced pressure to give the title compound (3 mg).

Workup

  1. stirringthe resulting mixture was stirred at room temperature for 10 minutes
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with water and brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customthe solvent was removed under reduced pressure
  6. filtrationcollected by filtration
  7. washThe collected solids were washed with the same solvent
  8. customdried under reduced pressure

Sources & evidence

ORD record
ord-eb23e64303ae400c80c45aa72cdcafc0
Source dataset
uspto-grants-2012_07
Patent number
US08217069B2

Reaction notes

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