Dichloromethane → HCID 18980339, compound
Reaction equation
C([O:3][C:4]([C:6]1[N:15]=[C:14]([NH:16][CH2:17][C:18]2[CH:23]=[CH:22][C:21]3[O:24][CH2:25][O:26][C:20]=3[CH:19]=2)[C:13]2[C:8](=[CH:9][CH:10]=[C:11](Cl)[CH:12]=2)[N:7]=1)=O)C.C(Cl)[Cl:29].O1CCCC1.[H-].C([Al+]CC(C)C)C(C)C>C1(C)C=CC=CC=1.CO>[CH:4]([C:6]1[N:15]=[C:14]([NH:16][CH2:17][C:18]2[CH:23]=[CH:22][C:21]3[O:24][CH2:25][O:26][C:20]=3[CH:19]=2)[C:13]2[C:8](=[C:9]([Cl:29])[CH:10]=[CH:11][CH:12]=2)[N:7]=1)=[O:3]Participants
7
Procedure
0.50 g (0.0013 mol) of 2-ethoxycarbonyl-4-(3,4-methylenedioxybenzyl)amino-6-chloroquinazoline was dissolved in a solvent mixture comprising 20 ml of methylene chloride and 20 ml of tetrahydrofuran. 2.6 ml of a 1.0M solution of diisobutylaluminum hydride in toluene was dropped into the solution prepared above at -78° C. under stirring. The obtained mixture was stirred at -78° C. for several hours, followed by the addition of 20 ml of methanol. The obtained mixture was distilled under a reduced pressure to remove the solvent. The residue was purified by silica gel column chromatography and recrystallized from ethyl acetate/n-hexane to give 0.23 g of the title compound as a pale-yellow crystal.
Workup
- customprepared above at -78° C.
- stirringThe obtained mixture was stirred at -78° C. for several hours
- distillationThe obtained mixture was distilled under a reduced pressure
- customto remove the solvent
- customThe residue was purified by silica gel column chromatography
- customrecrystallized from ethyl acetate/n-hexane
Sources & evidence
- ORD record
- ord-b51894dc936346e9af7f3d0d48f7e1e9
- Source dataset
- uspto-grants-1998_09
- Patent number
- US05801180
Reaction notes
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