Reaction #2398

Reaction equation

2-{6-chloro-5-(4-methylphenyl)pyrimidin-4-yloxy}-ethanol

sodium azide

dimethyformamide

→

2-{6-azido-5-(4-methylphenyl)pyrimidin-4-yloxy}ethanol

Yield 87.5%

Solvents

water

Conditions

Workup

1. 1
   Temperatureis heated
2. 2
   TemperatureAfter cooling
3. 3
   Extractionextracted with ethyl acetate
4. 4
   WashThe ethyl acetate layer is washed
5. 5
   Otherdried
6. 6
   Otherevaporated
7. 7
   Otherto remove the solvent
8. 8
   OtherThe residue is crystallized from hexane

Procedure

A mixture of 2-{6-chloro-5-(4-methylphenyl)pyrimidin-4-yloxy}-ethanol (21.85 g), sodium azide (10.7 g) and dimethyformamide (260 ml) is heated with stirring at 75°-80° C. overnight. After cooling, the mixture is treated with water, and extracted with ethyl acetate. The ethyl acetate layer is washed, dried, and evaporated to remove the solvent. The residue is crystallized from hexane to give 2-{6-azido-5-(4-methylphenyl)pyrimidin-4-yloxy}ethanol (19.6 g).

Source