Reaction #4009

Reaction equation

2-amino-4-chloro-6-chloromethylpyrimidine

potassium t-butoxide

n-butanol

→

2-amino-4-n-butoxy-6-chloromethylpyrmidine

Conditions

Workup

1. 1
   TemperatureAfter this time, the solution was cooled
2. 2
   Otherevaporated in vacuo
3. 3
   OtherThe residue was partitioned between ethyl acetate and water
4. 4
   Otherthe organic phase was separated
5. 5
   Washwashed three times with water
6. 6
   Dryingthen dried (MgSO4)
7. 7
   OtherEvaporation of the solvent
8. 8
   Othergave the crude product which
9. 9
   Otherwas purified by chromatography on silica (Merck Kieselgel 60)
10. 10
    Washeluted with ether

Procedure

3,56 Parts of 2-amino-4-chloro-6-chloromethylpyrimidine and 2.24 parts of potassium t-butoxide were dissolved in 60 parts of n-butanol at room temperature then the solution was heated at 50° C. for 2 hours, with stirring. After this time, the solution was cooled and evaporated in vacuo. The residue was partitioned between ethyl acetate and water and the organic phase was separated and washed three times with water then dried (MgSO4). Evaporation of the solvent gave the crude product which was purified by chromatography on silica (Merck Kieselgel 60) eluted with ether to give 2-amino-4-n-butoxy-6-chloromethylpyrmidine as an oil.

Source