Floxuridine → HCID 18646874, compound

HRID 728202Notes

Reaction equation

HRID 728202 reaction equation
[H-].[Na+].[F:3][C:4]1[C:5](=[O:19])[NH:6][C:7](=[O:18])[N:8]([CH:17]=1)[C@@H:9]1[O:16][C@H:13]([CH2:14][OH:15])[C@@H:11]([OH:12])[CH2:10]1.Cl[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=1>CS(C)=O>[F:3][C:4]1[C:5](=[O:19])[NH:6][C:7](=[O:18])[N:8]([CH:17]=1)[C@@H:9]1[O:16][C@H:13]([CH2:14][OH:15])[C@@H:11]([O:12][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=2)[CH2:10]1.[F:3][C:4]1[C:5](=[O:19])[NH:6][C:7](=[O:18])[N:8]([CH:17]=1)[C@@H:9]1[O:16][C@H:13]([CH2:14][O:15][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=2)[C@@H:11]([OH:12])[CH2:10]1

Participants

6

Reactant 3

HCID 5790FloxuridineHCID 79772-ChloropyridineHCID 24758Sodium hydride

Product 2

HCID 18646874HCID 18646874, compoundHCID 18646875HCID 18646875, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A 0.70 g quantity of sodium hydride (60%, dispersion in mineral oil) was added to a solution of 2.00 g of 2'-deoxy-5-fluorouridine in 10 ml of dimethyl sulfoxide. The mixture was stirred at room temperature for 30 minutes. To the mixture was added 0.91 ml of 2-chloropyridine. Then the mixture was stirred at 80° C. for 3 hours. The solvent was distilled off and the residue was dissolved in 50 ml of ethyl acetate and 30 ml of water. The solution was made into a weak acidic solution by addition of 6N-hydrochloric acid. The ethyl acetate layer was separated, washed with water, dried over anhydrous magnesium sulfate and concentrated. The residue was purified by silica gel column chromatography using 1- 2% methanol-chloroform as an eluent, giving 2'-deoxy3',5'-0-di-(2-pyridyl)-5-fluorouridine (Example 46), 2'-deoxy-5-fluoro-3'-O-(2-pyridyl)uridine (Example 47) and 2'-deoxy-5-fluoro- 5'-O-(2-pyridyl)uridine (Example 48).

Workup

  1. stirringThen the mixture was stirred at 80° C. for 3 hours
  2. distillationThe solvent was distilled off
  3. dissolutionthe residue was dissolved in 50 ml of ethyl acetate
  4. additionThe solution was made into a weak acidic solution by addition of 6N-hydrochloric acid
  5. customThe ethyl acetate layer was separated
  6. washwashed with water
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated
  9. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-7cf8f354407a448fae8b7b51b238a0ae
Source dataset
uspto-grants-1991_09
Patent number
US05047521

Reaction notes

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