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

HRID 248762
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HRID 248762 반응식
[CH3:1][O:2][N:3]=[C:4]([CH3:17])[CH2:5][N:6]1C(=O)C2=CC=CC=C2C1=O.O.NN.Cl[C:22]1[N:30]=[CH:29][N:28]=[C:27]2[C:23]=1[NH:24][CH:25]=[N:26]2.C(N(C(C)C)C(C)C)C>CO.O.CCOCC>[CH3:1][O:2][N:3]=[C:4]([CH3:17])[CH2:5][NH:6][C:22]1[N:30]=[CH:29][N:28]=[C:27]2[C:23]=1[NH:24][CH:25]=[N:26]2
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참가 물질

8

반응물 4

HCID 24654Hydrazine hydrate (1:1)HCID 81531DiisopropylethylamineHCID 53592776-ChloropurineHCID 85669803N-[2-(N-methoxyimino)propyl]phthalimide

생성물 1

HCID 85669800N6-[2-(N-methoxyimino)propyl]adenine수율 21.4%

시약·촉매·용매 3

HCID 887Methanol
용매
HCID 962Water용매
HCID 3283Diethyl Ether용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-be9bea7af4784ec6b8ed99483d40a265
출처 데이터셋
uspto-grants-1993_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05211738

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