Water → 2-(6-Azidopyrimidin-4-yloxy)ethanol

HRID 1082308Notes

Reaction equation

HRID 1082308 reaction equation
Cl[C:2]1[N:7]=[CH:6][N:5]=[C:4]([O:8][CH2:9][CH2:10][OH:11])[CH:3]=1.[N-:12]=[N+:13]=[N-:14].[Na+].O>CN(C)C=O>[N:12]([C:2]1[N:7]=[CH:6][N:5]=[C:4]([O:8][CH2:9][CH2:10][OH:11])[CH:3]=1)=[N+:13]=[N-:14]

Participants

5

Reactant 3

HCID 962WaterHCID 33557Sodium AzideHCID 125648862-[(6-Chloropyrimidin-4-yl)oxy]ethan-1-ol

Product 1

HCID 189310712-(6-Azidopyrimidin-4-yloxy)ethanolYield 28.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 2-(6-chloropyrimidin-4-yloxy)ethanol (5.61 g) in dimethylformamide (60 ml) is added sodium azide (4.18 g), and the mixture is stirred at 70° C. for 20 hours. After cooling, the reaction solution is treated with water, and extracted with ethyl acetate. The ethyl acetate layer is dried, and evaporated to remove the solvent. The residue is purified by silica gel column chromatography (solvent; hexane/ethyl acetate=1:1) to give 2-(6-azidopyrimidin-4-yloxy)ethanol (1.68 g).

Workup

  1. temperatureAfter cooling
  2. extractionextracted with ethyl acetate
  3. dry with materialThe ethyl acetate layer is dried
  4. customevaporated
  5. customto remove the solvent
  6. customThe residue is purified by silica gel column chromatography (solvent; hexane/ethyl acetate=1:1)

Sources & evidence

ORD record
ord-26c514975a574b5aa294bf0b1a9e1c82
Source dataset
uspto-grants-1996_12
Patent number
US05589478

Reaction notes

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