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

HRID 2216965Notes

Reaction equation

HRID 2216965 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH:18]([CH3:19])[C:17]3[C:12](=[N:13][C:14]([NH:20][C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)=[N:15][CH:16]=3)[N:11]([C:27]3[CH:28]=[C:29]([CH:32]=[CH:33][CH:34]=3)[C:30]#[N:31])[C:10]2=[O:35])=[CH:5][CH:4]=1.[OH-:36].[Na+].OO>CS(C)=O>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([N:9]2[CH:18]([CH3:19])[C:17]3[C:12](=[N:13][C:14]([NH:20][C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)=[N:15][CH:16]=3)[N:11]([C:27]3[CH:28]=[C:29]([CH:32]=[CH:33][CH:34]=3)[C:30]([NH2:31])=[O:36])[C:10]2=[O:35])=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 10367082(+/-)-3-[3-(4-methoxy-phenyl)-4-methyl-2-oxo-7-phenylamino-3,4-dihydro-2H-pyrimido[4,5-d]pyrimidin-1-yl]-benzonitrile

Product 1

HCID 10480299(+/-)-3-[3-(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

A solution of (±)-3-[3-(4-methoxy-phenyl)-4-methyl-2-oxo-7-phenylamino-3,4-dihydro-2H-pyrimido[4,5-d]pyrimidin-1-yl]-benzonitrile (0.11 g; 0.22 mmol) (from Example 5b supra) in dimethyl sulfoxide (1.5 mL) was cooled in an ice-water bath. Aqueous sodium hydroxide (1.0 M; 0.38 mL; 0.38 mmol) was added, followed by aqueous hydrogen peroxide (30% solution; 70 μL; 0.69 mmol). The cooling bath was removed following the additions and the mixture was stirred at room temperature for 3 hours. The solid was collected and washed with water and hot dichloromethane. This crude material was purified by flash chromatography (Biotage; 12M; 99:1 to 80:20 ethyl acetate-methanol gradient) and the pure product crystallized out of solution upon concentration to give (±)-3-[3-(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 64.6 mg; 57.9%). Melting Point: 268–273° C. (discolored on melting).

Workup

  1. customThe cooling bath was removed
  2. customThe solid was collected
  3. washwashed with water and hot dichloromethane
  4. customThis crude material was purified by flash chromatography (Biotage; 12M; 99:1 to 80:20 ethyl acetate-methanol gradient)
  5. customthe pure product crystallized out of solution upon concentration

Sources & evidence

ORD record
ord-0c1f218f5ca14f8fbe7edd022864e296
Source dataset
uspto-grants-2006_09
Patent number
US07112676B2

Reaction notes

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