Triethylamine → HCID 23078350, compound

HRID 228891Notes

Reaction equation

HRID 228891 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([CH3:14])=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][N:3]=1.C(N(CC)CC)C>CN(C)C=O.[OH-].[Pd+2].[OH-]>[CH3:13][O:12][C:9]1[CH:10]=[C:11]2[C:6](=[CH:7][C:8]=1[CH3:14])[N:5]=[CH:4][N:3]=[CH:2]2

Participants

5

Procedure

4-Chloro-6-methoxy-7-methyl-quinazoline (99 mg) was dissolved in N,N-dimethylformamide (6 ml) to prepare a solution. Triethylamine (0.6 ml) and 20% palladium hydroxide (4 mg) were added to the solution, and the mixture was stirred under hydrogen pressure at room temperature overnight. The reaction solution was filtered through Celite and was then washed with chloroform and methanol, and the solvent was removed by distillation under the reduced pressure. Water was added to the residue, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was then washed with saturated brine and was 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 chloroform-methanol to give 6-methoxy-7-methyl-quinazoline (76 mg, yield 93%).

Workup

  1. customto prepare a solution
  2. filtrationThe reaction solution was filtered through Celite
  3. washwas then washed with chloroform and methanol
  4. customthe solvent was removed by distillation under the reduced pressure
  5. additionWater was added to the residue
  6. extractionthe mixture was extracted with ethyl acetate
  7. washThe ethyl acetate layer was then washed with saturated brine
  8. dry with materialwas 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-93e36d100dba4ffc9245cbd5cffb5b75
Source dataset
uspto-grants-2009_07
Patent number
US07560558B2

Reaction notes

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