Ammonia → HCID 21996901, compound

HRID 232517Notes

Reaction equation

HRID 232517 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

Procedure

9.8 g (0.578 mol) of gaseous ammonia were passed into a mixture of 62.5 g (0.289 mol) of 2,4-difluoro-6-chlorodifluoromethoxypyrimidine in 300 ml of tetrahydrofuran in the course of one hour at from -75° to -70° C. while stirring. Stirring was continued for one hour at -70° C., after which the mixture was heated to room temperature. The precipitate which separated out was filtered off under suction and partitioned between ethyl acetate and water, and the organic phase was dried over magnesium sulfate. The reaction filtrate was evaporated down, the residue was dissolved in the above ethyl acetate phase and the solution was chromatographed over silica gel using 5:1 petroleum ether/ether and was evaporated down. 46.5 g (75.3% of theory) of the title compound were obtained as colorless crystals of melting point 77°-80° C.

Workup

  1. stirringStirring
  2. customThe precipitate which separated out
  3. filtrationwas filtered off under suction
  4. custompartitioned between ethyl acetate and water
  5. dry with materialthe organic phase was dried over magnesium sulfate
  6. customThe reaction filtrate was evaporated down
  7. dissolutionthe residue was dissolved in the above ethyl acetate phase
  8. customthe solution was chromatographed over silica gel using 5:1 petroleum ether/ether
  9. customwas evaporated down

Sources & evidence

ORD record
ord-e0b2f6116c904b29aedcd868a2202b07
Source dataset
uspto-grants-1997_01
Patent number
US05591694

Reaction notes

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