9-(2,3,5-Tri-O-benzyl-beta-D-arabinofuranosyl)-2-fluoroadenine → Fludarabine

HRID 487719

Reaktionsgleichung

Reaktionsgleichung von HRID 487719
C([O:8][C@H:9]1[C@H:13]([O:14]CC2C=CC=CC=2)[C@@H:12]([CH2:22][O:23]CC2C=CC=CC=2)[O:11][C@H:10]1[N:31]1[CH:39]=[N:38][C:37]2[C:32]1=[N:33][C:34]([F:41])=[N:35][C:36]=2[NH2:40])C1C=CC=CC=1>[Pd](Cl)Cl>[C@@H:10]1([N:31]2[CH:39]=[N:38][C:37]3[C:32]2=[N:33][C:34]([F:41])=[N:35][C:36]=3[NH2:40])[O:11][C@H:12]([CH2:22][OH:23])[C@@H:13]([OH:14])[C@@H:9]1[OH:8]

Komponenten

3

Edukt 1

HCID 109627089-(2,3,5-Tri-O-benzyl-beta-D-arabinofuranosyl)-2-fluoroadenine

Produkt 1

HCID 657237FludarabineAusbeute 66 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 24290Palladium ChlorideKatalysator

Versuchsvorschrift

Compound (VI) (3.6 mmole) and palladium chloride (1.4 g, 7.9 mmole) were used as in Example 1. The pressure was about 35 psig. The reaction was complete in about 1 hour and gave a 66% yield of product (VII). The amount of catalyst was 70% by weight or 2.2 moles per mole of (VI). The yield was not optimal and there was a risk of defluorination of (VI). Too much catalyst was necessary.

Quellen und Nachweise

ORD-Eintrag
ord-f322ed31d48441659e25a1236629ea32
Quelldatensatz
uspto-grants-1994_03
Patentnummer
US05296589

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