Hydrazine hydrate (1:1) → 2-(9H-Purin-6-ylamino)acetaldehyde O-methyloxime

HRID 248760Notes

Reaction equation

HRID 248760 reaction equation
[CH3:1][O:2][N:3]=[CH:4][CH2:5]C1C=CC=C2C(NC(=O)C=12)=O.O.NN.Cl[C:21]1[N:29]=[CH:28][N:27]=[C:26]2[C:22]=1[NH:23][CH:24]=[N:25]2.C([N:32](C(C)C)C(C)C)C>C(O)C.CCOCC>[CH3:1][O:2][N:3]=[CH:4][CH2:5][NH:32][C:21]1[N:29]=[CH:28][N:27]=[C:26]2[C:22]=1[NH:23][CH:24]=[N:25]2

Participants

7

Reactant 4

HCID 24654Hydrazine hydrate (1:1)HCID 81531DiisopropylethylamineHCID 53592776-ChloropurineHCID 86746841HCID 86746841, compound

Product 1

HCID 856697992-(9H-Purin-6-ylamino)acetaldehyde O-methyloximeYield 2%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 3283Diethyl EtherSolvent

Procedure

0.290 g (1.33 mmol) of N-[(2-(N-methoxyimino)ethyl]phthalimide was dissolved in 8 ml of ethanol and to the solution was added 77.7 μl (1.60 mmol) of hydrazine hydrate, followed by being refluxed for 5 hours. The reaction mixture was cooled to room temperature and then, 15 ml of ether was added thereto and the mixture was left to stand at 0° C. for 1 hour to sufficiently precipitate solids. The solids were removed by suction filtration and the filtrate was dried over sodium sulfate and concentrated to 1 ml by an avaporator. This concentrated filtrate was dissolved in 5 ml of isopropanol and to the solution were added 77.7 mg (0.503 mmol) of 6-chloropurine and 88 μl of ethyldiisopropylamine, followed by being refluxed with heating on an oil bath for 5 hours. The precipitated crystals were collected by filtration and thereafter, were purified by a thin layer chromatography (silica gel, developing agent: 10% ethanolchloroform) to give 5.2 mg (yield 2%) of the titled compound as a white powder.

Workup

  1. temperatureby being refluxed for 5 hours
  2. waitthe mixture was left
  3. customThe solids were removed by suction filtration
  4. dry with materialthe filtrate was dried over sodium sulfate
  5. concentrationconcentrated to 1 ml by an avaporator
  6. dissolutionThis concentrated filtrate was dissolved in 5 ml of isopropanol and to the solution
  7. temperatureby being refluxed
  8. temperaturewith heating on an oil bath for 5 hours
  9. filtrationThe precipitated crystals were collected by filtration
  10. customwere purified by a thin layer chromatography (silica gel, developing agent: 10% ethanolchloroform)

Sources & evidence

ORD record
ord-1fdd20e830574783b80282e307c35db7
Source dataset
uspto-grants-1993_05
Patent number
US05211738

Reaction notes

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