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

HRID 1247649Notes

Reaction equation

HRID 1247649 reaction equation
[CH3:1][N:2]([CH3:40])[CH2:3][CH2:4][C:5]1[CH:6]=[C:7]([NH:11][C:12]2[N:17]=[C:16]3[N:18]([C:32]4[CH:33]=[C:34]([CH:37]=[CH:38][CH:39]=4)[C:35]#[N:36])[C:19](=[O:31])[N:20]([C:23]4[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=4)[CH:21]([CH3:22])[C:15]3=[CH:14][N:13]=2)[CH:8]=[CH:9][CH:10]=1.[OH-:41].[Na+].C(#N)C1C=CC=CC=1.OO>CS(C)=O>[CH3:40][N:2]([CH3:1])[CH2:3][CH2:4][C:5]1[CH:6]=[C:7]([NH:11][C:12]2[N:17]=[C:16]3[N:18]([C:32]4[CH:33]=[C:34]([CH:37]=[CH:38][CH:39]=4)[C:35]([NH2:36])=[O:41])[C:19](=[O:31])[N:20]([C:23]4[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=4)[CH:21]([CH3:22])[C:15]3=[CH:14][N:13]=2)[CH:8]=[CH:9][CH:10]=1

Participants

6

Reactant 4

HCID 784Hydrogen PeroxideHCID 7505Benzonitrile2×HCID 14798Sodium HydroxideHCID 10052823(+/-)-3-[7-[3-(2-dimethylamino-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 10325293(+/-)-3-[7-[3-(2-dimethylamino-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 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

(±)-3-[7-[3-(2-Dimethylamino-ethyl)-phenylamino]-3-(4-methoxy-phenyl)-4-methyl-2-oxo-3,4-dihydro-2H-pyrimido[4,5-d]pyrimidin-1-yl]-benzonitrile (92.7 mg; 0.17 mmol) (from Example 6 supra) was dissolved in dimethyl sulfoxide (1.0 mL) and the resulting solution was cooled in an ice-water bath. Aqueous sodium hydroxide (1 M; 300 μL; 0.30 mmol) was added, resulting in the precipitation of the benzonitrile. Aqueous hydrogen peroxide (30%; 53 μL; 0.52 mmol) was then added. The benzonitrile went back into solution and the product then precipitate out of solution. After 4 hours, the reaction was diluted with water. The solid was collected, washed with water and dried. Recrystallization from dichloromethane-ether gave (±)-3-[7-[3-(2-dimethylamino-ethyl)-phenylamino]-3-(4-methoxy-phenyl)-4-methyl-2-oxo-3,4-dihydro-2H-pyrimido[4,5-d]pyrimidin-1-yl]-benzamide. (Yield 72.9 mg; 76.1%). Melting Point: 215–230° C. HR-MS(ES+) m/z Calculated for C31H33N7O3 ([M+H]+): 552.2718; Found: 552.2722.

Workup

  1. temperaturethe resulting solution was cooled in an ice-water bath
  2. customthe product then precipitate out of solution
  3. additionthe reaction was diluted with water
  4. customThe solid was collected
  5. washwashed with water
  6. customdried
  7. customRecrystallization from dichloromethane-ether

Sources & evidence

ORD record
ord-3bc21b781d964d6a95e4a46d76221f19
Source dataset
uspto-grants-2006_10
Patent number
US07129351B2

Reaction notes

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