Water → HCID 22248392, compound
Reaction equation
[C:1]([O:5][C:6]1[C:11]([C:12](OCC)=[O:13])=[CH:10][N:9]=[CH:8][N:7]=1)([CH3:4])([CH3:3])[CH3:2].[H-].C([Al+]CC(C)C)C(C)C.C(C(C(C([O-])=O)O)O)([O-])=O.[Na+].[K+].O>C1(C)C=CC=CC=1.C(OCC)(=O)C>[C:1]([O:5][C:6]1[C:11]([CH:12]=[O:13])=[CH:10][N:9]=[CH:8][N:7]=1)([CH3:4])([CH3:2])[CH3:3]Participants
7
Conditions
- Temperature
- -78 °C
Procedure
After dissolving 976 mg of ethyl 4-tert-butoxypyrimidine-5-carboxylate in 15 ml of toluene, the solution was cooled to −78° C. 3.2 ml of diisobutylaluminium hydride (1.5 M, toluene solution) was added dropwise while stirring, and then after 30 minutes, an aqueous solution of potassium sodium (+)-tartrate was added and the mixture was stirred at room temperature. Water was added to the reaction solution and extraction was performed with ethyl acetate. The organic layer was washed with water and saturated brine in that order and dried over anhydrous magnesium sulfate, and then the solvent was distilled off under reduced pressure to obtain 0.85 g of crude 4-tert-butoxypyrimidine-5-carboxaldehyde.
Workup
- stirringthe mixture was stirred at room temperature
- washThe organic layer was washed with water and saturated brine in that order
- dry with materialdried over anhydrous magnesium sulfate
- distillationthe solvent was distilled off under reduced pressure
Sources & evidence
- ORD record
- ord-0de7dbae9e8649488024389144dd4d0c
- Source dataset
- uspto-grants-2006_02
- Patent number
- US06995144B2
Reaction notes
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