Ammonium Hydroxide → Uridine, 2′,5′-dideoxy-2′-fluoro-

HRID 2227205Notes

Reaction equation

HRID 2227205 reaction equation
I[CH2:2][C@H:3]1[O:7][C@@H:6]([N:8]2[CH:15]=[CH:14][C:12](=[O:13])[NH:11][C:9]2=[O:10])[C@H:5]([F:16])[C@@H:4]1[OH:17].[OH-].[NH4+].[H][H]>C(O)C.[Pd]>[F:16][C@@H:5]1[C@H:4]([OH:17])[C@@H:3]([CH3:2])[O:7][C@H:6]1[N:8]1[CH:15]=[CH:14][C:12](=[O:13])[NH:11][C:9]1=[O:10]

Participants

6

Reactant 3

HCID 14923Ammonium HydroxideHCID 66802808HCID 66802808, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 57259416Uridine, 2′,5′-dideoxy-2′-fluoro-

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

2′,5′-Dideoxy-5′-iodo-2′-fluorouridine (2.9, 8.1 mmoles) was dissolved in 95% ethanol (25 mL). Ammonium hydroxide (1.1 mL, 16.2 mmoles, 2 eq.) was added followed by 10% Pd/C (Aldrich, 0.1 g). Reaction under 50 psi hydrogen was carried out for 5 hours. The mixture was filtered and the pH adjusted to 7 with 1N HCl. The solvents were removed in vacuo and the residue dissolved in water. The product was extracted with ethyl acetate (3×). The ethyl acetate solution was dried with MgSO4, filtered, and the solvent removed in vacuo. The residue was purified by chromatography on 100 g of silica gel eluted with ethyl acetate. The product containing fractions were combined and the solvents removed in vacuo. The yield was 1.1 g, 58%. MS (APCl(−)): m/z (rel. intensity) 229 (100%, M−); 1H NMR (DMSO-d6) δ7.54 (d, 1H, H6, J=8 Hz), 5.76 (d, 1H, H-1′, J=22 Hz), 5.59 (d,1H, H5, J=8 Hz), 5.55 (d, 1H, OH, J=6 Hz), 5.05 (d, 1H, H-2′, J=53 Hz), 3.8 (m, 2H), 1.27 (d, 3H, H-5′, J=6 Hz).

Workup

  1. filtrationThe mixture was filtered
  2. customThe solvents were removed in vacuo
  3. dissolutionthe residue dissolved in water
  4. extractionThe product was extracted with ethyl acetate (3×)
  5. dry with materialThe ethyl acetate solution was dried with MgSO4
  6. filtrationfiltered
  7. customthe solvent removed in vacuo
  8. customThe residue was purified by chromatography on 100 g of silica gel
  9. washeluted with ethyl acetate
  10. additionThe product containing fractions
  11. customthe solvents removed in vacuo

Sources & evidence

ORD record
ord-3fd8329fe8ab4d5e81df6e678f6c2715
Source dataset
uspto-grants-2002_07
Patent number
US06413938B1

Reaction notes

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