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

HRID 229062Notes

Reaction equation

HRID 229062 reaction equation
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

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
130 °C

Procedure

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%).

Workup

  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

Sources & evidence

ORD record
ord-220946721a4e4461bb7f87f2277b68fe
Source dataset
uspto-grants-2009_07
Patent number
US07560558B2

Reaction notes

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