Water → Tert-butyl 3-(5-bromopyrimidin-2-yl)oxy-2,2-dimethylpropanoate
Reaction equation
[Br:1][C:2]1[CH:3]=C[C:5](Cl)=[N:6][CH:7]=1.[OH:9][CH2:10][C:11]([CH3:20])([CH3:19])[C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13].[H-].[Na+].O.C[N:25](C)C=O>>[Br:1][C:2]1[CH:7]=[N:6][C:5]([O:9][CH2:10][C:11]([CH3:20])([CH3:19])[C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])=[N:25][CH:3]=1Participants
Conditions
- Temperature
- 50 °C
Procedure
In N,N-dimethylformamide (10 mL) were dissolved 5-bromo-2-chloropyridine (1000 mg) and tert-butyl 3-hydroxy-2,2-dimethylpropanoate (991 mg), and 60% sodium hydride (248 mg) was added to the solution under ice-cooling. The reaction mixture was stirred at room temperature for 6 hours, at 50° C. for 1 hour and 45 minutes, and then, at room temperature overnight. Water was added to the reaction mixture under ice-cooling, and the mixture was extracted with ether. The organic layer was separated, washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=100:0 to 95:5) to obtain tert-butyl 3-(5-bromopyrimidin-2-yl)oxy-2,2-dimethylpropanoate (1.048 g).
Workup
- additionwas added to the solution under ice-
- temperaturecooling
- customat room temperature
- customovernight
- temperaturecooling
- extractionthe mixture was extracted with ether
- customThe organic layer was separated
- washwashed with saturated brine
- dry with materialdried over anhydrous magnesium sulfate
- concentrationconcentrated under reduced pressure
- customThe obtained residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=100:0 to 95:5)
Sources & evidence
- ORD record
- ord-61eabace70ee45f9a9f7eb6bdf4c80ca
- Source dataset
- uspto-grants-2016_04
- Patent number
- US09302996B2
Reaction notes
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