6-Azido-2-fluoro-9-(2,3,5-tri-O-benzyl-beta-D-arabinofuranosyl)purine → Fludarabine

HRID 1646667

Reaction equation

HRID 1646667 reaction equation
[N:1]([C:4]1[N:12]=[C:11]([F:13])[N:10]=[C:9]2[C:5]=1[N:6]=[CH:7][N:8]2[C@@H:14]1[O:34][C@H:33]([CH2:35][O:36]CC2C=CC=CC=2)[C@@H:24]([O:25]CC2C=CC=CC=2)[C@@H:15]1[O:16]CC1C=CC=CC=1)=[N+]=[N-]>COCCO.[Pd](Cl)Cl>[C@@H:14]1([N:8]2[CH:7]=[N:6][C:5]3[C:9]2=[N:10][C:11]([F:13])=[N:12][C:4]=3[NH2:1])[O:34][C@H:33]([CH2:35][OH:36])[C@@H:24]([OH:25])[C@@H:15]1[OH:16]

Participants

4

Reactant 1

HCID 544897616-Azido-2-fluoro-9-(2,3,5-tri-O-benzyl-beta-D-arabinofuranosyl)purine

Product 1

HCID 657237FludarabineYield 67.6%

Reagents, catalysts & solvents 2

HCID 24290Palladium ChlorideCatalystHCID 80192-MethoxyethanolSolvent

Procedure

6-Azido-2-fluoro-9-(2,3,5-tri-O-benzyl-β-D-arabinofuranosyl)purine (0.19 g) was dissolved in 2-methoxyethanol (20 mL) with palladium (II) chloride (PdCl2) (20 mg) and activated carbon and the mixture was hydrogenated at 55 pounds per square inch (psi) in a Parr shaker. The reaction was monitored by thin layer chromatography (TLC) until complete. The mixture was then filtered through celite and the filtrate was concentrated in vacuo. Three times, the residue was dissolved in ethanol and reconcentrated. Then the residue was recrystalized from ethanol/water to obtain 0.063 g of the title compound which was consistent in its structure with an authentic sample by IR and TLC.

Workup

  1. filtrationThe mixture was then filtered through celite
  2. concentrationthe filtrate was concentrated in vacuo
  3. dissolutionThree times, the residue was dissolved in ethanol
  4. customThen the residue was recrystalized from ethanol/water

Sources & evidence

ORD record
ord-4d0b759483994145a1322818e9484f05
Source dataset
uspto-grants-1993_01
Patent number
US05180824

Linked notes

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