Hydrazine hydrate (1:1) → N6-[2-(N-methoxyimino)propyl]adenine

0.232 g (1.00 mmol) of N-[2-(N-methoxyimino)propyl]phthalimide was dissolved in 6 ml of methanol and to the solution was added 60 μl (1.2 mmol) of hydrazine hydrate, followed by being refluxed for 5 hours. The reaction mixture was cooled to room temperature and then, 20 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 evaporator. This concentrated filtrate was dissolved in 5 ml of isopropanol and to the solution were added 105 mg (0.680 mmol) of 6-chloropurine and 101 μl of ethyldiisopropylamine, followed by being refluxed with heating on an oil bath for 5 hours. The reaction mixture was poured into 20 ml of water and extracted with chloroform (15 ml×5). The extract was dried over magnesium sulfate and the solvent was distilled off. The residue was purified by a thin layer chromatography (silica gel, developing agent: 15% ethanol-chloroform) to give 32.0 mg (yield 15%) of the titled compound as white solids.

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 evaporator
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. extractionextracted with chloroform (15 ml×5)
10. dry with materialThe extract was dried over magnesium sulfate
11. distillationthe solvent was distilled off
12. customThe residue was purified by a thin layer chromatography (silica gel, developing agent: 15% ethanol-chloroform)

ORD record

ord-be9bea7af4784ec6b8ed99483d40a265

Source dataset

uspto-grants-1993_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05211738