Sodium Azide → 9-(3-Azidopropyl)adenine

HRID 1896073Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1896073
Cl[CH2:2][CH2:3][CH2:4][N:5]1[CH:13]=[N:12][C:11]2[C:6]1=[N:7][CH:8]=[N:9][C:10]=2[NH2:14].[N-:15]=[N+:16]=[N-:17].[Na+]>CN(C=O)C>[N:15]([CH2:2][CH2:3][CH2:4][N:5]1[CH:13]=[N:12][C:11]2[C:6]1=[N:7][CH:8]=[N:9][C:10]=2[NH2:14])=[N+:16]=[N-:17]

Komponenten

4

Edukt 2

HCID 33557Sodium AzideHCID 2865919-(3-chloropropyl)-9H-purin-6-amine

Produkt 1

HCID 120978459-(3-Azidopropyl)adenineAusbeute 81 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A mixture of 9-(3-chloropropyl)adenine (1.9 g, 9 mM) and sodium azide (1.75 g, 27 mM) in DMF was stirred at 80° C. for 24 hours, cooled to room temperature, and filtered. The solid was washed with CH2Cl2. The solvent was removed from the combined filtrates and the residue was taken up in water with sonication. The aqueous layer was extracted with CH2Cl2 (3×60 mL). After removing solvent, the crude product was recrystallized from ethanol to give 9-(3-azidopropyl)adenine as a white crystalline solid in 81% yield.

Aufarbeitung

  1. temperaturecooled to room temperature
  2. filtrationfiltered
  3. washThe solid was washed with CH2Cl2
  4. customThe solvent was removed from the combined filtrates
  5. customthe residue was taken up in water with sonication
  6. extractionThe aqueous layer was extracted with CH2Cl2 (3×60 mL)
  7. customAfter removing solvent
  8. customthe crude product was recrystallized from ethanol

Quellen und Nachweise

ORD-Eintrag
ord-9dacc5f48ae04200906f46dae239581e
Quelldatensatz
uspto-grants-2013_08
Patentnummer
US08518885B2

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