Dimethyl Sulfoxide → 6,7-Dimethoxy-4-(5,6,5'-trimethyl-[2,2']bipyridin-3-yloxy)-quinazoline

HRID 229062노트

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HRID 229062 반응식
CS(C)=O.[CH3:5][C:6]1[CH:7]=[C:8]([OH:20])[C:9]([C:13]2[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][N:14]=2)=[N:10][C:11]=1[CH3:12].Cl[C:22]1[C:31]2[C:26](=[CH:27][C:28]([O:34][CH3:35])=[C:29]([O:32][CH3:33])[CH:30]=2)[N:25]=[CH:24][N:23]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>O>[CH3:33][O:32][C:29]1[CH:30]=[C:31]2[C:26](=[CH:27][C:28]=1[O:34][CH3:35])[N:25]=[CH:24][N:23]=[C:22]2[O:20][C:8]1[C:9]([C:13]2[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][N:14]=2)=[N:10][C:11]([CH3:12])=[C:6]([CH3:5])[CH:7]=1

참가 물질

6

반응물 4

HCID 679Dimethyl SulfoxideHCID 10796Cesium carbonateHCID 27693644-Chloro-6,7-dimethoxyquinazolineHCID 1363851085,6,5'-Trimethyl-[2,2']bipyridin-3-ol

생성물 1

HCID 577564026,7-Dimethoxy-4-(5,6,5'-trimethyl-[2,2']bipyridin-3-yloxy)-quinazoline수율 91%

시약·촉매·용매 1

HCID 962Water용매

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온도
130 °C

실험 절차

Dimethyl sulfoxide (1.4 ml) was added to 5,6,5′-trimethyl-[2,2′]bipyridin-3-ol (30 mg), 4-chloro-6,7-dimethoxyquinazoline (94 mg), and cesium carbonate (137 mg), and the mixture was stirred at 130° C. for 4 hr. The reaction solution was cooled to room temperature, water was then added to the reaction solution, the mixture was filtered, and the residue was washed with chloroform/methanol. The solvent was removed from the filtrate by distillation under the reduced pressure, water was added to the residue, and the mixture was extracted with chloroform. The chloroform layer was washed with water and was then dried over anhydrous sodium sulfate. The solvent was removed by distillation under the reduced pressure, and the residue was purified by thin layer chromatography using hexane-acetone to give the title compound (51 mg, yield 91%).

후처리

  1. temperatureThe reaction solution was cooled to room temperature
  2. filtrationthe mixture was filtered
  3. washthe residue was washed with chloroform/methanol
  4. customThe solvent was removed from the filtrate by distillation under the reduced pressure, water
  5. additionwas added to the residue
  6. extractionthe mixture was extracted with chloroform
  7. washThe chloroform layer was washed with water
  8. dry with materialwas then dried over anhydrous sodium sulfate
  9. customThe solvent was removed by distillation under the reduced pressure
  10. customthe residue was purified by thin layer chromatography

출처 및 근거

ORD 기록
ord-220946721a4e4461bb7f87f2277b68fe
출처 데이터셋
uspto-grants-2009_07
특허 번호
US07560558B2

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