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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 2216965
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HRID 2216965 반응식
[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
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 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

생성물 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

시약·촉매·용매 1

HCID 679
Dimethyl Sulfoxide
용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-0c1f218f5ca14f8fbe7edd022864e296
출처 데이터셋
uspto-grants-2006_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07112676B2

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