Hydrogen Peroxide → HCID 11189285, compound

HRID 1243214Notes

Reaction equation

HRID 1243214 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH2:18][C:17]3[C:12](=[N:13][C:14]([NH:19][C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)=[N:15][CH:16]=3)[N:11]([CH2:26][CH2:27][C:28]#[N:29])[C:10]2=[O:30])=[CH:5][CH:4]=1.[OH-:31].[Na+].OO>CS(C)=O.C(OCC)(=O)C>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH2:18][C:17]3[C:12](=[N:13][C:14]([NH:19][C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)=[N:15][CH:16]=3)[N:11]([CH2:26][CH2:27][C:28]([NH2:29])=[O:31])[C:10]2=[O:30])=[CH:5][CH:4]=1

Participants

6

Reactant 3

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 11281029HCID 11281029, compound

Product 1

HCID 11189285HCID 11189285, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To the solution of 3-[-3-(4-methoxy-phenyl)-2-oxo-7-phenylamino-3,4-dihydro-1H-pyrimido[4,5-d]pyrimidin-1-yl]-propionitrile (60 mg, 0.15 mmol) (from Example 26 supra) in dimethyl sulfoxide (2 mL) at 0 C was added 1.0 N aqueous sodium hydroxide solution (0.42 mL, 0.42 mmol) followed by 35% aqueous hydrogen peroxide (0.35 mL) (Fisher). The reaction mixture was stirred at 0° C. for 2 hours and then at room temperature overnight. The reaction was diluted with ethyl acetate (50 mL) and washed with water (3×20 mL). The organic layer was washed with brine (10 mL) and dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure to give the crude solid (71 mg) which was purified by recrystallization from hexanes-ethyl acetate to give 3-[-3-(4-methoxy-phenyl)-2-oxo-7-phenylamino-3,4-dihydro-1H-pyrimido[4,5-d]pyrimidin-1-yl]-propionamide as a gray solid. (Yield 28.3 mg, 45.1%).

Workup

  1. customat room temperature
  2. customovernight
  3. washwashed with water (3×20 mL)
  4. washThe organic layer was washed with brine (10 mL)
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customto give the crude solid (71 mg) which
  9. customwas purified by recrystallization from hexanes-ethyl acetate

Sources & evidence

ORD record
ord-1e9dae83a1f8469f97eee05070f190fe
Source dataset
uspto-grants-2006_10
Patent number
US07115740B2

Reaction notes

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