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

HRID 1292824Notes

Reaction equation

HRID 1292824 reaction equation
[BH4-].[Na+].[CH3:3][O:4][C:5]1[C:10]([CH:11]=[O:12])=[C:9]([C:13]([F:16])([F:15])[F:14])[N:8]=[CH:7][N:6]=1.O>CO>[CH3:3][O:4][C:5]1[C:10]([CH2:11][OH:12])=[C:9]([C:13]([F:15])([F:14])[F:16])[N:8]=[CH:7][N:6]=1

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 178628984-Methoxy-6-trifluoromethyl-pyrimidine-5-carbaldehyde

Product 1

HCID 17862874(4-Methoxy-6-trifluoromethylpyrimidin-5-yl)-methanolYield 32.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

0.24 g (6.3 mmoles) of sodium borohydride was gradually added, at room temperature, to a solution of 1.3 g (6.3 mmoles) of 4-methoxy-6-trifluoromethylpyrimidine-5-carboaldehyde dissolved in 30 ml of methanol. The mixture was stirred for 3 hours to give rise to a reaction. After confirmation of 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 water and an aqueous sodium chloride solution in this order and then dried over anhydrous magnesium sulfate. The resulting solution was subjected to vacuum distillation to remove the solvent contained therein. The residue was purified by silica gel column chromatography to obtain 0.42 g (yield: 32.1%) of (4-methoxy-6-trifluoromethylpyrimidin-5-yl)-methanol

Workup

  1. customto give rise
  2. customto a reaction
  3. customAfter confirmation of the completion of the reaction
  4. extractionfollowed by extraction with ethyl acetate
  5. washThe resulting organic layer was washed with water
  6. dry with materialan aqueous sodium chloride solution in this order and then dried over anhydrous magnesium sulfate
  7. distillationThe resulting solution was subjected to vacuum distillation
  8. customto remove the solvent
  9. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-3f723fec44d2464eba452656e0453f3f
Source dataset
uspto-grants-2007_07
Patent number
US07238689B2

Reaction notes

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