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

HRID 1978149Notes

Reaction equation

HRID 1978149 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

Conditions

Temperature
-70 °C

Procedure

8.7 g (0.51 mol) of gaseous ammonia were passed over the course of 1 hour into a stirred mixture of 51 g (0.255 mol) of 2,4-difluoro-6-trifluoromethoxypyrimidine and 200 ml of diethyl ether at −75 to −70° C. The mixture was stirred at −70° C. for 1½ hours and at room temperature for 1 hour and then concentrated under reduced pressure. The residue was taken up in methylene chloride and the organic phase was extracted with water, dried, concentrated and chromatographed on silica gel with 8:1 petroleum ether/ether, resulting in 38.1 g (75.6% of theory) of the title compound as colorless crystals of melting point 86-89° C.

Workup

  1. concentrationconcentrated under reduced pressure
  2. extractionthe organic phase was extracted with water
  3. customdried
  4. concentrationconcentrated
  5. customchromatographed on silica gel with 8:1 petroleum ether/ether

Sources & evidence

ORD record
ord-6523778846f241c7875d7ff72c390cf0
Source dataset
uspto-grants-2001_05
Patent number
US06235904B1

Reaction notes

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