Reaction #2408

Reaction equation

water

2-(6-chloropyrimidin-4-yloxy)ethanol

sodium azide

→

2-(6-azidopyrimidin-4-yloxy)ethanol

Yield 28.9%

Solvents

dimethylformamide

Conditions

Workup

1. 1
   TemperatureAfter cooling
2. 2
   Extractionextracted with ethyl acetate
3. 3
   DryingThe ethyl acetate layer is dried
4. 4
   Otherevaporated
5. 5
   Otherto remove the solvent
6. 6
   OtherThe residue is purified by silica gel column chromatography (solvent; hexane/ethyl acetate=1:1)

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).

Source