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

HRID 1247648Notes

Reaction equation

HRID 1247648 reaction equation
[CH2:1]([N:3]([CH2:41][CH3:42])[CH2:4][CH2:5][C:6]1[CH:7]=[C:8]([NH:12][C:13]2[N:18]=[C:17]3[N:19]([C:33]4[CH:34]=[C:35]([CH:38]=[CH:39][CH:40]=4)[C:36]#[N:37])[C:20](=[O:32])[N:21]([C:24]4[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][CH:25]=4)[CH:22]([CH3:23])[C:16]3=[CH:15][N:14]=2)[CH:9]=[CH:10][CH:11]=1)[CH3:2].[OH-:43].[Na+].C(#N)C1C=CC=CC=1.OO>CS(C)=O.O>[CH2:41]([N:3]([CH2:1][CH3:2])[CH2:4][CH2:5][C:6]1[CH:7]=[C:8]([NH:12][C:13]2[N:18]=[C:17]3[N:19]([C:33]4[CH:34]=[C:35]([CH:38]=[CH:39][CH:40]=4)[C:36]([NH2:37])=[O:43])[C:20](=[O:32])[N:21]([C:24]4[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][CH:25]=4)[CH:22]([CH3:23])[C:16]3=[CH:15][N:14]=2)[CH:9]=[CH:10][CH:11]=1)[CH3:42]

Participants

7

Reactant 4

HCID 784Hydrogen PeroxideHCID 7505Benzonitrile2×HCID 14798Sodium HydroxideHCID 10076529(+/-)-3-[7-[3-(2-diethylamino-ethyl)-phenylamino]-3-(4-methoxy-phenyl)-4-methyl-2-oxo-3,4-dihydro-2H-pyrimido[4,5-d]pyrimidin-1-yl]-benzonitrile

Product 1

HCID 11757931(+/-)-3-[7-[3-(2-diethylamino-ethyl)-phenylamino]-3-(4-methoxy-phenyl)-4-methyl-2-oxo-3,4-dihydro-2H-pyrimido[4,5-d]pyrimidin-1-yl]-benzamide

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

(±)-3-[7-[3-(2-Diethylamino-ethyl)-phenylamino]-3-(4-methoxy-phenyl)-4-methyl-2-oxo-3,4-dihydro-2H-pyrimido[4,5-d]pyrimidin-1-yl]-benzonitrile (0.35 g; 0.60 mmol) (from Example 5b supra) was dissolved in dimethyl sulfoxide (3.5 mL) and the resulting solution was cooled in an ice-water bath. Aqueous sodium hydroxide (1 M; 1.15 mL; 1.15 mmol) was added, resulting in the precipitation of the benzonitrile. Aqueous hydrogen peroxide (30%; 195 μL; 1.91 mmol) was then added. The benzonitrile slowly went back into solution. After 3 hours, water was added to the reaction mixture. The product initially separated out as a gum which then solidified. The solid was collected, washed with water and dried. Recrystallization from dichloromethane-ether gave (±)-3-[7-[3-(2-diethylamino-ethyl)-phenylamino]-3-(4-methoxy-phenyl)-4-methyl-2-oxo-3,4-dihydro-2H-pyrimido[4,5-d]pyrimidin-1-yl]-benzamide. (Yield 0.30 g; 84.8%).

Workup

  1. temperaturethe resulting solution was cooled in an ice-water bath
  2. customThe product initially separated out as a gum which
  3. customThe solid was collected
  4. washwashed with water
  5. customdried
  6. customRecrystallization from dichloromethane-ether

Sources & evidence

ORD record
ord-2feed68300c34ade850c02a83da3bbe4
Source dataset
uspto-grants-2006_10
Patent number
US07129351B2

Reaction notes

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