Ammonia → HCID 21996901, compound

HRID 2254847Notes

Reaction equation

HRID 2254847 reaction equation
[NH3:1].F[C:3]1[N:8]=[C:7]([F:9])[C:6]([O:10][CH:11]([F:13])[F:12])=[C:5]([Cl:14])[N:4]=1>O1CCCC1>[NH2:1][C:3]1[N:4]=[C:5]([Cl:14])[C:6]([O:10][CH:11]([F:13])[F:12])=[C:7]([F:9])[N:8]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 21996893HCID 21996893, compound

Product 1

HCID 21996901HCID 21996901, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-70 °C

Procedure

9.8 g (0.578 mol) of gaseous ammonia were passed over the course of one hour into a stirred mixture of 62.5 g (0.289 mol) of 2,4-difluoro-6-chlorodifluoromethoxypyrimidine and 300 ml of tetrahydrofuran at -75 to -70° C. The mixture was stirred at -70° C. for one hour and then warmed to room temperature. The precipitate was filtered off with suction and partitioned between ethyl acetate and water, and the organic phase was dried over magnesium sulfate, filtered and concentrated. The residue was dissolved in ethyl acetate, chromatographed on silica gel with 5:1 petroleum ether/ether and concentrated. 46.5 g (75.3% of theory) of the title compound were obtained as colorless crystals of melting point 77°-80° C.

Workup

  1. temperaturewarmed to room temperature
  2. filtrationThe precipitate was filtered off with suction
  3. custompartitioned between ethyl acetate and water
  4. dry with materialthe organic phase was dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. dissolutionThe residue was dissolved in ethyl acetate
  8. customchromatographed on silica gel with 5:1 petroleum ether/ether
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-9281575a386f48ac8f0f5a381843d5cc
Source dataset
uspto-grants-1993_08
Patent number
US05237063

Reaction notes

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