Trifluoroacetic acid → 3-(2-Chloro-6,7-dimethoxyquinazolin-4-yl)phenylamine
Reaction equation
[Cl:1][C:2]1[N:11]=[C:10]([C:12]2[CH:13]=[C:14]([NH:18]C(=O)OC(C)(C)C)[CH:15]=[CH:16][CH:17]=2)[C:9]2[C:4](=[CH:5][C:6]([O:28][CH3:29])=[C:7]([O:26][CH3:27])[CH:8]=2)[N:3]=1.FC(F)(F)C(O)=O.[OH-].[Na+]>>[Cl:1][C:2]1[N:11]=[C:10]([C:12]2[CH:13]=[C:14]([NH2:18])[CH:15]=[CH:16][CH:17]=2)[C:9]2[C:4](=[CH:5][C:6]([O:28][CH3:29])=[C:7]([O:26][CH3:27])[CH:8]=2)[N:3]=1Participants
4
Conditions
- Temperature
- 5 °C
Procedure
Under a nitrogen atmosphere, 420 mg (1.00 mmol) of t-butyl [3-(2-chloro-6,7-dimethoxyquinazolin-4-yl)phenyl]carbamate was allowed to cool down to 5° C., trifluoroacetic acid (1 mL) was added dropwise while stirring, and the mixture was stirred at room temperature. The mixture was stirred for 1.25 hours, then allowed to cool down to 5° C. to 10° C., 2 N aqueous sodium hydroxide solution (6.2 mL) was added dropwise to precipitate pale yellow crystals. The mixture was stirred at room temperature for 15 minutes, and the precipitated crystals were filtration and dried to give 306 mg of a target product (yield: 95.6%).