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

HRID 254220Notes

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.C(OCC)(=O)C>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, into 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 and extraction with ethyl acetate was conducted. 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 reduced pressure 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
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 reduced pressure distillation
customto remove the solvent

Sources & evidence

ORD record: ord-1c3b755358e046fb958b833e20d42f07
Source dataset: uspto-grants-2011_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07875606B2

Reaction notes

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