Water → (4-Ethoxy-6-trifluoromethylpyrimidin-5-yl)-methanol

HRID 1292825Notes

Reaction equation

[CH2:1]([O:3][C:4]1[C:9]([CH:10]=[O:11])=[C:8]([C:12]([F:15])([F:14])[F:13])[N:7]=[CH:6][N:5]=1)[CH3:2].[BH4-].[Na+].O>CO>[CH2:1]([O:3][C:4]1[C:9]([CH2:10][OH:11])=[C:8]([C:12]([F:14])([F:15])[F:13])[N:7]=[CH:6][N:5]=1)[CH3:2]

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of 3.82 g (17.2 mmoles) of 4-ethoxy-6-trifluoromethylpyrimidine-5-carboaldehyde dissolved in 50 ml of methanol was added, with ice-cooling, to a solution of 1.7 g (45.7 mmoles) of sodium borohydride dissolved in 50 ml of methanol. The mixture was stirred at 0° C. for 1 hour to give rise to a reaction. After the completion of the reaction, the reaction mixture was poured into water, followed by extraction with ethyl acetate. The resulting organic layer was washed with an aqueous sodium chloride solution and then dried over anhydrous magnesium sulfate. The resulting solution was subjected to vacuum distillation to remove the solvent contained therein, to obtain 3.77 g (yield: 97.8%) of (4-ethoxy-6-trifluoromethylpyrimidin-5-yl)-methanol

Workup

additionwas added, with ice-
customto give rise
customto a reaction
customAfter the completion of the reaction
extractionfollowed by extraction with ethyl acetate
washThe resulting organic layer was washed with an aqueous sodium chloride solution
dry with materialdried over anhydrous magnesium sulfate
distillationThe resulting solution was subjected to vacuum distillation
customto remove the solvent

Sources & evidence

ORD record: ord-1dca1db12fec49bcb7ba804f9161aaab
Source dataset: uspto-grants-2007_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07238689B2

Reaction notes

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