Triethylamine → HCID 23078350, compound
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]2Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 2
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
- customto prepare a solution
- filtrationThe reaction solution was filtered through Celite
- washwas then washed with chloroform and methanol
- customthe solvent was removed by distillation under the reduced pressure
- additionWater was added to the residue
- extractionthe mixture was extracted with ethyl acetate
- washThe ethyl acetate layer was then washed with saturated brine
- dry with materialwas dried over anhydrous sodium sulfate
- customThe solvent was removed by distillation under the reduced pressure
- 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
Loading…