Reaction #4007

Reaction equation

2-amino-4-chloromethyl-6-methoxypyrimidine

caesium fluoride

→

2-amino-4-fluoromethyl-6-methoxypyrimidine

Solvents

dimethylformamide

Conditions

Workup

1. 1
   Temperatureunder reflux for 2 hours
2. 2
   TemperatureThe mixture was cooled
3. 3
   Otherevaporated in vacuo
4. 4
   Washthe solution was washed four times with water
5. 5
   DryingThe organic phase was dried with anhydrous magnesium sulphate
6. 6
   workup.STIRRINGstirred with decolourising charcoal
7. 7
   Filtrationfiltered
8. 8
   Otherevaporated
9. 9
   OtherThe crude product was purified by chromatography on silica
10. 10
    Washeluted with ethyl acetate

Procedure

A mixture of 17.0 parts of 2-amino-4-chloromethyl-6-methoxypyrimidine, 59.5 parts of caesium fluoride and 130 parts of dry dimethylformamide was stirred under reflux for 2 hours. The mixture was cooled and evaporated in vacuo. The residue was taken up in ethyl acetate and the solution was washed four times with water. The organic phase was dried with anhydrous magnesium sulphate, stirred with decolourising charcoal, filtered and evaporated. The crude product was purified by chromatography on silica, eluted with ethyl acetate to give 2-amino-4-fluoromethyl-6-methoxypyrimidine m.p. 119°-121° C.

Source