Reaction #319556

ord-65ef55b7962348c491271d3593de0b82

Reaction equation

CCc1cn([C@@H]2O[C@H](CN=[N+]=[N-])[C@@H](O)[C@@H]2F)c(=O)[nH]c1=O
1-(5-azido-2,5-dideoxy-2-fluoro-β-D-arabinofuranosyl)-5-ethyluracil
→
CCc1cn([C@@H]2O[C@H](CN)[C@@H](O)[C@@H]2F)c(=O)[nH]c1=O
1-(5-amino-2,5-dideoxy-2-fluoro-β-D-arabinofuranosyl)-5-ethyluracil
Yield 82.1%

Reactants

CCc1cn([C@@H]2O[C@H](CN=[N+]=[N-])[C@@H](O)[C@@H]2F)c(=O)[nH]c1=O
1-(5-azido-2,5-dideoxy-2-fluoro-β-D-arabinofuranosyl)-5-ethyluracil

Reagents

[Pd]
palladium-on-carbon

Solvents

CCO
ethanol

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    OtherThe catalyst was removed by filtration
  2. 2
    Otherthe filtrate was evaporated
  3. 3
    OtherThe residue was triturated with diethyl ether
  4. 4
    Otherthe solid was removed by filtration
  5. 5
    Washwashed with ethyl acetate
  6. 6
    Otherdried in vacuo

Procedure

A solution of 0.4 g of 1-(5-azido-2,5-dideoxy-2-fluoro-β-D-arabinofuranosyl)-5-ethyluracil in 20 ml of ethanol was hydrogenated at room temperature and under atmospheric pressure in the presence of 0.1 g of 10% palladium-on-carbon catalyst for 24 hours. The catalyst was removed by filtration and the filtrate was evaporated. The residue was triturated with diethyl ether and the solid was removed by filtration, washed with ethyl acetate and dried in vacuo to give 0.3 g of 1-(5-amino-2,5-dideoxy-2-fluoro-β-D-arabinofuranosyl)-5-ethyluracil as a white solid.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US04851519uspto-grants-1989_07