Water → (2-Phenylpyrimidin-5-yl)methanol

HRID 914475Notes

Reaction equation

HRID 914475 reaction equation
[C:1]1([C:7]2[N:12]=[CH:11][C:10]([CH:13]=[O:14])=[CH:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[BH4-].[Na+].O>C(O)C>[C:1]1([C:7]2[N:12]=[CH:11][C:10]([CH2:13][OH:14])=[CH:9][N:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 962WaterHCID 8201352-Phenylpyrimidine-5-carbaldehydeHCID 4311764Sodium borohydride

Product 1

HCID 21298145(2-Phenylpyrimidin-5-yl)methanolYield 86.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

2-Phenylpyrimidine-5-carbaldehyde (2.0 g) was dissolved in ethanol (20 mL), sodium tetrahydroborate (411 mg) was added under ice-cooling, and the mixture was stirred at 0° C. for 1 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated aqueous ammonium chloride solution and then saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to give the title compound (1.75 g) as a white solid.

Workup

  1. temperaturecooling
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with saturated aqueous ammonium chloride solution
  4. dry with materialsaturated brine, and dried over anhydrous sodium sulfate
  5. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-b38dc111e46e4ec1a82e5f9793846de7
Source dataset
uspto-grants-2011_09
Patent number
US08026370B2

Reaction notes

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