Triethylamine → 2-Ethoxy-4-fluoro-6-hydrazinylpyrimidine

HRID 864626Notes

Reaction equation

HRID 864626 reaction equation
[CH2:1]([O:3][C:4]1[N:9]=[C:8]([F:10])[CH:7]=[C:6](F)[N:5]=1)[CH3:2].C(N(CC)CC)C.O.[NH2:20][NH2:21].NN>O.C(#N)C>[CH2:1]([O:3][C:4]1[N:9]=[C:8]([F:10])[CH:7]=[C:6]([NH:20][NH2:21])[N:5]=1)[CH3:2]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 9321HydrazineHCID 24654Hydrazine hydrate (1:1)HCID 110409852-Ethoxy-4,6-difluoropyrimidine

Product 1

HCID 109429042-Ethoxy-4-fluoro-6-hydrazinylpyrimidine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
10 °C

Procedure

A mixture of 100 g of 94 percent purity (0.59 mol) 2-ethoxy-4,6-difluoropyrimidine, 275 mL of acetonitrile, and 107 g of water was prepared and cooled to 10° C. To this was added 68 g (0.67 mol) of triethylamine and then 34 g (0.68 mol) of hydrazine hydrate, slowly with stirring and cooling (at 5° to 10° C). When all of the hydrazine had been added, the mixture was stirred another 15 min with cooling and was then allowed to warm. After a total of 1 hour, the solids that formed were recovered by vacuum filtration and were washed twice with 100 mL portions of water and then with 50 mL of ethanol. The title compound, which was obtained as a white solid melting at 141°-143° C., amounted to 79.7 g (80 percent of theory).

Workup

  1. customwas prepared
  2. temperaturecooling (at 5° to 10° C)
  3. temperaturewith cooling
  4. temperatureto warm
  5. customAfter a total of 1 hour, the solids that formed
  6. filtrationwere recovered by vacuum filtration
  7. washwere washed twice with 100 mL portions of water

Sources & evidence

ORD record
ord-cf0fe4eecffe4cad9682fbff2cfe7843
Source dataset
uspto-grants-1996_10
Patent number
US05563269

Reaction notes

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