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

Participants

Reaction Steps

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.

Provenance & Evidence