Sodium borohydride → 1-(6-Chloropyrimidin-4-yl)ethanol

HRID 2401190Notes

Reaction equation

HRID 2401190 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]([C:8](=[O:10])[CH3:9])[CH:3]=1.[BH4-].[Na+]>C(O)C>[Cl:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]([CH:8]([OH:10])[CH3:9])[CH:3]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 722142471-(6-Chloropyrimidin-4-yl)ethan-1-one2×

Product 1

HCID 838541011-(6-Chloropyrimidin-4-yl)ethanolYield 79.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1-(6-Chloro-4-pyrimidinyl)ethanone (Intermediate 18A, 1.0 g, 6.39 mmol) was dissolved in ethanol (21 mL), treated with sodium borohydride (0.242 g, 6.39 mmol) and the resulting mixture was stirred at room temperature under argon for 2 hours. The solvent was removed under reduced pressure and the residue was diluted with water and extracted with ethyl acetate (×3). The ethyl acetate layers were combined, dried under magnesium sulfate and evaporated under reduced pressure to give the title compound as a yellow oil (808 mg);

Workup

  1. customThe solvent was removed under reduced pressure
  2. additionthe residue was diluted with water
  3. extractionextracted with ethyl acetate (×3)
  4. customdried under magnesium sulfate
  5. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-e2acdec75d9640a7ac4fac48b35ea0e7
Source dataset
uspto-grants-2014_08
Patent number
US08796283B2

Reaction notes

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