Cesium fluoride → 2-Amino-4-fluoromethyl-6-methoxypyrimidine

HRID 3911

Reaction equation

HRID 3911 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([CH2:8]Cl)[CH:5]=[C:4]([O:10][CH3:11])[N:3]=1.[F-:12].[Cs+]>CN(C)C=O>[NH2:1][C:2]1[N:7]=[C:6]([CH2:8][F:12])[CH:5]=[C:4]([O:10][CH3:11])[N:3]=1

Participants

4

Reactant 2

HCID 25953Cesium fluorideHCID 138848154-(Chloromethyl)-6-methoxypyrimidin-2-amine

Product 1

HCID 201534972-Amino-4-fluoromethyl-6-methoxypyrimidine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

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.

Workup

  1. temperatureunder reflux for 2 hours
  2. temperatureThe mixture was cooled
  3. customevaporated in vacuo
  4. washthe solution was washed four times with water
  5. dry with materialThe organic phase was dried with anhydrous magnesium sulphate
  6. stirringstirred with decolourising charcoal
  7. filtrationfiltered
  8. customevaporated
  9. customThe crude product was purified by chromatography on silica
  10. washeluted with ethyl acetate

Sources & evidence

ORD record
ord-57c87955e9ed4a11aa4e6f98c7716c2b
Source dataset
uspto-grants-1988_02
Patent number
US04723006

Linked notes

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