Dichloromethane → 2-[2-(N,N-diethylamino)ethyl]-4-(3,4-dimethoxyphenyl)-6,7-dimethoxyquinazoline
Reaction equation
Br[CH2:2][CH2:3][C:4]1[N:13]=[C:12]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[C:16]([O:22][CH3:23])[CH:15]=2)[C:11]2[C:6](=[CH:7][C:8]([O:26][CH3:27])=[C:9]([O:24][CH3:25])[CH:10]=2)[N:5]=1.[CH2:28]([NH:30][CH2:31][CH3:32])[CH3:29].ClCCl>O>[CH2:28]([N:30]([CH2:2][CH2:3][C:4]1[N:13]=[C:12]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[C:16]([O:22][CH3:23])[CH:15]=2)[C:11]2[C:6](=[CH:7][C:8]([O:26][CH3:27])=[C:9]([O:24][CH3:25])[CH:10]=2)[N:5]=1)[CH2:31][CH3:32])[CH3:29]Participants
5
Procedure
A mixture of 2-(2-bromoethyl)-4-(3,4-dimethoxyphenyl)-6,7-dimethoxyquinazoline (0.486 g), diethylamine (0.41 g) and dichloromethane (10 ml) was stirred under reflux for 6 hours. The reaction mixture was poured into water and extracted with dichloromethane. The dichloromethane layer was washed with water and dried over magnesium sulfate, and the solvent was evaporated. The residue was subjected to column chromatography on silica gel. The fractions eluted with chloroform-ethyl acetate (1/1, v/v) gave 2-[2-(N,N-diethylamino)ethyl]-4-(3,4-dimethoxyphenyl)-6,7-dimethoxyquinazoline (0.040 g, 8%) which was then recrystallized from ethyl acetate-hexane. Colorless prisms. mp. 164°-166° C.
Workup
- temperatureunder reflux for 6 hours
- extractionextracted with dichloromethane
- washThe dichloromethane layer was washed with water
- dry with materialdried over magnesium sulfate
- customthe solvent was evaporated
- washThe fractions eluted with chloroform-ethyl acetate (1/1
Sources & evidence
- ORD record
- ord-7428576384904210ac958682fce66b5f
- Source dataset
- uspto-grants-1998_12
- Patent number
- US05852039
Reaction notes
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