Ammonium Chloride → 1-(2-Aminopyrimidin-4-yl)ethanol

HRID 1845861Notes

Reaction equation

HRID 1845861 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([C:8](=[O:10])[CH3:9])[CH:5]=[CH:4][N:3]=1.[BH4-].[Na+].[Cl-].[NH4+]>CO>[NH2:1][C:2]1[N:7]=[C:6]([CH:8]([OH:10])[CH3:9])[CH:5]=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 135822701-(2-Aminopyrimidin-4-yl)ethan-1-one2×

Product 1

HCID 672548751-(2-Aminopyrimidin-4-yl)ethanolYield 53.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

1-(2-aminopyrimidin-4-yl)ethanone (Compound 3a) (0.5 g) was dissolved in 50 mL methanol and cooled to 0° C. Sodium borohydride (0.138 g) was added portion wise and the mixture was stirred for 16 hours at room temperature. Saturated ammonium chloride solution (20 mL) was added and this mixture was extracted twice with ethyl acetate. The combined organic layers were washed with brine, dried over sodium sulfate and evaporated to give the title compound (270 mg) as a colourless oil that solidified on standing.

Workup

  1. extractionthis mixture was extracted twice with ethyl acetate
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over sodium sulfate
  4. customevaporated

Sources & evidence

ORD record
ord-d4e5eedf93cc4a08aed9cd57ee5105c9
Source dataset
uspto-grants-2015_02
Patent number
US08952001B2

Reaction notes

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