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

HRID 232518Notes

Reaction equation

HRID 232518 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, the residue was taken up in methylene chloride and the solution was extracted with water. After the organic phase had been dried, evaporated down and chromatographed over silica gel using 8:1 petroleum ether/ether, 38.1 g (75.6% of theory) of the title compound were obtained 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. extractionthe solution was extracted with water
  6. customAfter the organic phase had been dried
  7. customevaporated down
  8. customchromatographed over silica gel using 8:1 petroleum ether/ether, 38.1 g (75.6% of theory) of the title compound
  9. customwere obtained as colorless crystals of melting point 86°-89° C.

Sources & evidence

ORD record
ord-bff6f921969442869d097fe364d5a0a4
Source dataset
uspto-grants-1997_01
Patent number
US05591694

Reaction notes

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