Pyridine, hydrofluoride (1:1) → 2'Fluoro-2'-deoxyuridine

HRID 1871858Notes

Reaction equation

HRID 1871858 reaction equation
[CH:1]1[C:15](=[O:16])[N:14]=[C:13]2[N:3]([C@@H:4]3[O:8][C@H:7]([CH2:9][OH:10])[C@@H:6]([OH:11])[C@@H:5]3[O:12]2)[CH:2]=1.C1C=CN=CC=1.[FH:23]>O1CCOCC1>[F:23][C@@H:5]1[C@H:6]([OH:11])[C@@H:7]([CH2:9][OH:10])[O:8][C@H:4]1[N:3]1[CH:2]=[CH:1][C:15](=[O:16])[NH:14][C:13]1=[O:12]

Participants

4

Reactant 2

HCID 64774Pyridine, hydrofluoride (1:1)HCID 8061382,2'-Anhydrouridine

Product 1

HCID 1508512'Fluoro-2'-deoxyuridineYield 75%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

2,2'-Cyclouridine is treated with a solution of 70% hydrogen fluoride/pyridine in dioxane at 120° C. for ten hours to provide after solvent removal a 75% yield of 2'-deoxy-2'-fluorouridine. The 5'-DMT and 3'-cyanoethoxydiisopropyl-phosphoramidite derivitized nucleoside is obtained by standard literature procedures (Gait, Ed., Oligonucleotide Synthesis. A Practical Approach, IRL Press, Washington, DC (1984)], or according to the procedure of Example 4-a.

Workup

  1. customto provide

Sources & evidence

ORD record
ord-2a7ef372124d418e819eedefb897f3a8
Source dataset
uspto-grants-2000_08
Patent number
US06107094

Reaction notes

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