2-(6-Azidopyrimidin-4-yloxy)ethanol → 2-((6-Aminopyrimidin-4-yl)oxy)ethanol

HRID 1082309Notes

Reaction equation

HRID 1082309 reaction equation
[N:1]([C:4]1[N:9]=[CH:8][N:7]=[C:6]([O:10][CH2:11][CH2:12][OH:13])[CH:5]=1)=[N+]=[N-]>[C].[Pd].C(O)C>[NH2:1][C:4]1[N:9]=[CH:8][N:7]=[C:6]([O:10][CH2:11][CH2:12][OH:13])[CH:5]=1

Participants

4

Reactant 1

HCID 189310712-(6-Azidopyrimidin-4-yloxy)ethanol

Product 1

HCID 189310692-((6-Aminopyrimidin-4-yl)oxy)ethanolYield 79%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

A mixture of 2-(6-azidopyrimidin-4-yloxy)ethanol (1.64 g), 10% palladium-carbon (0.25 g) and ethanol (20 ml) is subjected to catalytic hydrogenation at room temperature for one hour under hydrogen atmosphere (1 atm). The catalyst is removed by filtration, and the filtrate is concentrated. The residue is recrystallized from ethanol/diethyl ether to give 2-(6-aminopyrimidin-4-yloxy)ethanol (1.11 g).

Workup

  1. customThe catalyst is removed by filtration
  2. concentrationthe filtrate is concentrated
  3. customThe residue is recrystallized from ethanol/diethyl ether

Sources & evidence

ORD record
ord-0eb6c2ed3c334b04b66fc6a9c275e67d
Source dataset
uspto-grants-1996_12
Patent number
US05589478

Reaction notes

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