HCID 18633461, compound → HCID 15460476, compound

HRID 232374Notes

Reaction equation

HRID 232374 reaction equation
[N:1]([CH2:4][C@H:5]1[O:9][C@@H:8]([N:10]2[CH:17]=[C:16]([CH2:18][CH3:19])[C:14](=[O:15])[NH:13][C:11]2=[O:12])[C@@H:7]([F:20])[C@@H:6]1[OH:21])=[N+]=[N-]>C(O)C.[Pd]>[NH2:1][CH2:4][C@H:5]1[O:9][C@@H:8]([N:10]2[CH:17]=[C:16]([CH2:18][CH3:19])[C:14](=[O:15])[NH:13][C:11]2=[O:12])[C@@H:7]([F:20])[C@@H:6]1[OH:21]

Participants

4

Reactant 1

HCID 18633461HCID 18633461, compound

Product 1

HCID 15460476HCID 15460476, compoundYield 82.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

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.

Workup

  1. customThe catalyst was removed by filtration
  2. customthe filtrate was evaporated
  3. customThe residue was triturated with diethyl ether
  4. customthe solid was removed by filtration
  5. washwashed with ethyl acetate
  6. customdried in vacuo

Sources & evidence

ORD record
ord-65ef55b7962348c491271d3593de0b82
Source dataset
uspto-grants-1989_07
Patent number
US04851519

Reaction notes

Loading…