Ammonia → 2-Amino-4-fluoro-6-trifluoromethoxypyrimidine

HRID 1647677Notes

Reaction equation

HRID 1647677 reaction equation
[NH3:1].F[C:3]1[N:8]=[C:7]([F:9])[CH:6]=[C:5]([O:10][C:11]([F:14])([F:13])[F:12])[N:4]=1>C(OCC)C>[NH2:1][C:3]1[N:8]=[C:7]([F:9])[CH:6]=[C:5]([O:10][C:11]([F:14])([F:13])[F:12])[N:4]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 150227122,4-Difluoro-6-trifluoromethoxypyrimidine

Product 1

HCID 150227162-Amino-4-fluoro-6-trifluoromethoxypyrimidine

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

8.7 g (0.51 mol) of gaseous ammonia were passed into a mixture of 51 g (0.255 mol) of 2,4-difluoro-6-trifluoromethoxypyrimidine in 200 ml of diethyl ether in the course of 1 hour at from -75° to -70° C. while stirring. Stirring was continued for a further 11/2 hours at -70° C. and for 1 hour at room temperature. The reaction mixture was evaporated down under reduced pressure and the residue was taken up in methylene chloride and extracted with water. Drying the organic phase, evaporating down and chromatographing the residue over silica gel using 8:1 petroleum ether/ether gave 38.1 g (75.6% of theory) of the title compound as colorless crystals of melting point 86°-89° C.

Workup

  1. stirringStirring
  2. custom2 hours
  3. customat -70° C.
  4. customThe reaction mixture was evaporated down under reduced pressure
  5. extractionextracted with water
  6. customDrying the organic phase
  7. customevaporating down

Sources & evidence

ORD record
ord-9e9520d88ad64317bb0f656f90064e5f
Source dataset
uspto-grants-1995_07
Patent number
US05434124

Reaction notes

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