Hydrogen Peroxide → (+/-)-3-[3-(2-fluoro-4-methoxy-phenyl)-4-methyl-2-oxo-7-phenylamino-3,4-dihydro-2H-pyrimido[4,5-d]pyrimidin-1-yl]-benzamide

HRID 2216978Notes

Reaction equation

HRID 2216978 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][C:3]=1[N:10]1[CH:19]([CH3:20])[C:18]2[C:13](=[N:14][C:15]([NH:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[N:16][CH:17]=2)[N:12]([C:28]2[CH:29]=[C:30]([CH:33]=[CH:34][CH:35]=2)[C:31]#[N:32])[C:11]1=[O:36].[OH-:37].[Na+].OO.O>CS(C)=O>[F:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][C:3]=1[N:10]1[CH:19]([CH3:20])[C:18]2[C:13](=[N:14][C:15]([NH:21][C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=3)=[N:16][CH:17]=2)[N:12]([C:28]2[CH:29]=[C:30]([CH:33]=[CH:34][CH:35]=2)[C:31]([NH2:32])=[O:37])[C:11]1=[O:36]

Participants

6

Reactant 4

HCID 784Hydrogen PeroxideHCID 962WaterHCID 14798Sodium HydroxideHCID 10254568(+/-)-3-[3-(2-fluoro-4-methoxy-phenyl)-4-methyl-2-oxo-7-phenylamino-3,4-dihydro-2H-pyrimido[4,5-d]pyrimidin-1-yl]-benzonitrile

Product 1

HCID 10074627(+/-)-3-[3-(2-fluoro-4-methoxy-phenyl)-4-methyl-2-oxo-7-phenylamino-3,4-dihydro-2H-pyrimido[4,5-d]pyrimidin-1-yl]-benzamide

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

(±)-3-[3-(2-Fluoro-4-methoxy-phenyl)-4-methyl-2-oxo-7-phenylamino-3,4-dihydro-2H-pyrimido[4,5-d]pyrimidin-1-yl]-benzonitrile (0.80 g; 1.67 mmol) (from Example 9b supra) was dissolved in dimethyl sulfoxide (25 mL). Most of the material went into solution. Aqueous sodium hydroxide (1.0 N; 3.34 mL; 3.34 mmol) was added followed by hydrogen peroxide (30% in water; 0.51 mL, 4.99 mmol) at room temperature. After stirring for 45 minutes, water was added and a white solid precipitated out of solution. The solid was collected, washed with water and dried. Dissolution of the solid required significant volumes of dichloromethane-methanol-acetonitrile. The solvent mixture was then distilled off until solid began to crystallize out of solution. Cooling and filtration gave (±)-3-[3-(2-fluoro-4-methoxy-phenyl)-4-methyl-2-oxo-7-phenylamino-3,4-dihydro-2H-pyrimido[4,5-d]pyrimidin-1-yl]-benzamide as a white solid. (Yield 0.56 g; 67.6%).

Workup

  1. customa white solid precipitated out of solution
  2. customThe solid was collected
  3. washwashed with water
  4. customdried
  5. dissolutionDissolution of the solid required significant volumes of dichloromethane-methanol-acetonitrile
  6. distillationThe solvent mixture was then distilled off until solid
  7. customto crystallize out of solution
  8. temperatureCooling
  9. filtrationfiltration

Sources & evidence

ORD record
ord-5e02fffa284e4bfe93b8deef960877f0
Source dataset
uspto-grants-2006_09
Patent number
US07112676B2

Reaction notes

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