Water → Ethyl 2-[7-bromo-3-(4-bromo-2-fluorobenzyl)-1,2,3,4-tetrahydro-2,4-dioxoquinazolin-1-yl]acetate
Reaction equation
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:22])[N:7]([CH2:13][C:14]3[CH:19]=[CH:18][C:17]([Br:20])=[CH:16][C:15]=3[F:21])[C:8](=[O:12])[NH:9]2)=[CH:4][CH:3]=1.[H-].[Na+].Br[CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28].O>CN(C)C=O>[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:22])[N:7]([CH2:13][C:14]3[CH:19]=[CH:18][C:17]([Br:20])=[CH:16][C:15]=3[F:21])[C:8](=[O:12])[N:9]2[CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28])=[CH:4][CH:3]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a solution of 7-bromo-3-(4-bromo-2-fluorobenzyl)-1,2,3,4-tetrahydro-2,4-dioxoquinazoline (2.80 g) in N,N-dimethylformamide (56 ml) was added sodium hydride (60% in mineral oil, 334 mg) with stirring at 0° C. under an atmosphere of nitrogen and the mixture was stirred at room temperature for 1 hour. To this mixture was added ethyl bromoacetate (0.85 ml) dropwise and the mixture was stirred at room temperature for 2 hours. The solvent was removed under reduced pressure to give a residue, which was poured into water and extracted with ethyl acetate. The extract was washed with water and dried. Removal of the solvent followed by recrystallization from isopropyl either gave ethyl 2-[7-bromo-3-(4-bromo-2-fluorobenzyl)-1,2,3,4-tetrahydro-2,4-dioxoquinazolin-1-yl]acetate (3.11 g).
Workup
- stirringthe mixture was stirred at room temperature for 1 hour
- stirringthe mixture was stirred at room temperature for 2 hours
- customThe solvent was removed under reduced pressure
- customto give a residue, which
- extractionextracted with ethyl acetate
- washThe extract was washed with water
- customdried
- customRemoval of the solvent
- customfollowed by recrystallization from isopropyl
Sources & evidence
- ORD record
- ord-a284de40719a4165be417b80bd851f44
- Source dataset
- uspto-grants-1988_03
- Patent number
- US04734419
Reaction notes
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