Hydrazine → 2-Amino-4-hydroxy-6-hydrazinopyrimidine

HRID 2167929Notes

Reaction equation

HRID 2167929 reaction equation
[NH2:1][C:2]1[NH:7][C:6](=[O:8])[CH:5]=[C:4](Cl)[N:3]=1.[NH2:10][NH2:11]>O>[NH2:1][C:2]1[NH:7][C:6](=[O:8])[CH:5]=[C:4]([NH:10][NH2:11])[N:3]=1

Participants

4

Reactant 2

HCID 9321HydrazineHCID 1354033564-Pyrimidinol, 2-amino-6-chloro-

Product 1

HCID 1354719822-Amino-4-hydroxy-6-hydrazinopyrimidineYield 46%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A stirred suspension of 15.0 g (103 mmol) of 1 in 250 mL water was added 12 g (375 mmol) of anhydrous hydrazine, and the mixture was heated at reflux for 3 h. The resulting clear solution was cooled, and the precipitate which separated was collected by filtration, washed with water followed by ethanol and dried to give 6.6 g (46%) of white solid. mp decomposes at 313° C. (Literature mp 314-315° C., see Taylor, E. C.; Cocuzza, J. A. Synthesis and Properties of 7-Azaxanthopterin. J. Org. Chem. 1979, 44, 1125-1128).

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 3 h
  3. temperatureThe resulting clear solution was cooled
  4. customthe precipitate which separated
  5. filtrationwas collected by filtration
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-02acf632886349d2b2ab28ce82fda13b
Source dataset
uspto-grants-2015_06
Patent number
US09045489B2

Reaction notes

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