Ammonia → HCID 21996901, compound

HRID 1647676Notes

Reaction equation

HRID 1647676 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 at from -75° to -70° C. in the course of one hour while stirring. Stirring was continued for one hour at -70° C., after which the mixture was warmed up to room temperature. The precipitate which had separated out was filtered off under suction and partitioned between ethyl acetate and water and the organic phase was dried over mangesium sulfate. The reaction filtrate was evaporated down, the residue was dissolved in the above ethyl acetate phase, the solution was chromatographed over silica gel using 5:1 petroleum ether/ether and the eluate 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 had separated out
  3. filtrationwas filtered off under suction
  4. custompartitioned between ethyl acetate and water
  5. dry with materialthe organic phase was dried over mangesium 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. customthe eluate was evaporated down

Sources & evidence

ORD record
ord-fc112160fa3b4543a69e4b99d90b7b5c
Source dataset
uspto-grants-1995_07
Patent number
US05434124

Reaction notes

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