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Dimethyl Sulfoxide → 1-[2-[[3-(1,6-dihydro-6-oxo-9H-purin-9-yl)-1-oxopropyl]hydrazino]2-oxoethyl]pyridinium chloride

HRID 1534962
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1534962
[O:1]=[C:2]1[NH:10][CH:9]=[N:8][C:7]2[N:6]([CH2:11][CH2:12][C:13]([O:15]C3C=CC([N+]([O-])=O)=CC=3)=O)[CH:5]=[N:4][C:3]1=2.[CH:25]1[CH:30]=[CH:29][N+:28]([CH2:31][C:32]([NH:34][NH2:35])=[O:33])=[CH:27][CH:26]=1.[Cl-:36].CS(C)=O>C(#N)C>[Cl-:36].[O:1]=[C:2]1[NH:10][CH:9]=[N:8][C:7]2[N:6]([CH2:11][CH2:12][C:13]([NH:35][NH:34][C:32](=[O:33])[CH2:31][N+:28]3[CH:27]=[CH:26][CH:25]=[CH:30][CH:29]=3)=[O:15])[CH:5]=[N:4][C:3]1=2
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Komponenten

5

Edukt 3

HCID 679Dimethyl SulfoxideHCID 70773Pyridinioacetohydrazide chlorideHCID 1359739573-(1,6-dihydro-6-oxo-9H-purin-9-yl)propanoic acid, 4-nitrophenyl ester

Produkt 1

HCID 1364601101-[2-[[3-(1,6-dihydro-6-oxo-9H-purin-9-yl)-1-oxopropyl]hydrazino]2-oxoethyl]pyridinium chloride

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342
Acetonitrile
Lösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

0.300 g (0.9111 mmol) of 3-(1,6-dihydro-6-oxo-9H-purin-9-yl)propanoic acid, 4-nitrophenyl ester (AIT-0081) and 0.172 g (0.9166 mmol) of Girard's reagent P were placed into a 10 ml round bottom flask with 2 ml dimethylsulfoxide and a magnetic stirring bar. The solution was heated to 70° C. with stirring. As the solution began to warm up, the solids began to dissolve and the solution became progressively green in color. After about 30 minutes, the solution was completely homogeneous. The solution was allowed to react at 70° C. for four hours and was allowed to cool to room temperature. 10 ml acetonitrile was added and a white precipitate formed immediately. The solution was filtered and washed with acetonitrile and ether. The solid was allowed to dry but it absorbed H2O from the atmosphere. The hygroscopic effect could either be due to residual dimethylsulfoxide or the product itself.

Aufarbeitung

  1. temperatureto warm up
  2. dissolutionto dissolve
  3. customto react at 70° C. for four hours
  4. temperatureto cool to room temperature
  5. customa white precipitate formed immediately
  6. filtrationThe solution was filtered
  7. washwashed with acetonitrile and ether
  8. customto dry
  9. customit absorbed H2O from the atmosphere

Quellen und Nachweise

ORD-Eintrag
ord-701d6b56668c4f0cbdcfe0dd396b74e2
Quelldatensatz
uspto-grants-1992_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05091432

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