Water → HCID 22248392, compound

HRID 914870Notes

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

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-5571415ea730484a8dabe1bdc39b17a8
Source dataset: uspto-grants-2007_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07265108B2

Reaction notes

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