Hydrazine hydrate (1:1) → 4-Chloro-2-ethyl-6-hydrazinylpyrimidine

HRID 485499Notes

Reaction equation

HRID 485499 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6](Cl)[N:5]=[C:4]([CH2:9][CH3:10])[N:3]=1.O.[NH2:12][NH2:13]>CO>[Cl:1][C:2]1[CH:7]=[C:6]([NH:12][NH2:13])[N:5]=[C:4]([CH2:9][CH3:10])[N:3]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 5184654,6-Dichloro-2-ethylpyrimidine

Product 1

HCID 133936134-Chloro-2-ethyl-6-hydrazinylpyrimidineYield 86.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred, cold (0° C.) solution of 60 g (0.34 mole) of 4,6-dichloro-2-ethylpyrimidine in 500 ml of methanol was added 35 g (0.7 mole) of hydrazine hydrate while maintaining the temperature below 10° C. Stirring was continued for 2 hours after completion of the addition, the temperature being maintained at 0° C. The mixture was allowed to warm to about 20° C. and was stirred for 16 hours. The white solid was collected by filtration and the filtrate was partially evaporated to provide a second crop. The combined solids were washed with water and air dried to provide 51 g (77%) of 4-chloro-2-ethyl-6-hydrazinylpyrimidine, m.p. 147°-150° C.

Workup

  1. temperaturewhile maintaining the temperature below 10° C
  2. additionafter completion of the addition
  3. temperatureto warm to about 20° C.
  4. stirringwas stirred for 16 hours
  5. filtrationThe white solid was collected by filtration
  6. customthe filtrate was partially evaporated
  7. customto provide a second crop
  8. washThe combined solids were washed with water and air
  9. customdried

Sources & evidence

ORD record
ord-56d90b3dee97441f8a5edc1f4d815fb8
Source dataset
uspto-grants-1985_08
Patent number
US04536579

Reaction notes

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