Acetic Anhydride → 3'-Azido-5-Bromo-2'-Deoxyuridine

HRID 1885524Notes

Reaction equation

HRID 1885524 reaction equation
[N:1]([C@@:4]1([OH:19])[C@@H:8]([CH2:9][OH:10])[O:7][C@@H:6]([N:11]2[CH:18]=[CH:17][C:15](=[O:16])[NH:14][C:12]2=[O:13])[CH2:5]1)=[N+:2]=[N-:3].C(OC(=O)C)(=O)C.[Br:27]Br>C(O)(=O)C>[N:1]([C@@:4]1([OH:19])[C@@H:8]([CH2:9][OH:10])[O:7][C@@H:6]([N:11]2[CH:18]=[C:17]([Br:27])[C:15](=[O:16])[NH:14][C:12]2=[O:13])[CH2:5]1)=[N+:2]=[N-:3]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 24408BromineHCID 544067393'-Azido-2'-deoxyuridine

Product 1

HCID 539281813'-Azido-5-Bromo-2'-Deoxyuridine

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

3'-Azido-5-bromo-2'-doxyuridine was prepared from the known 3'-azido-2'-deoxyuridine (T. A. Krenitsky, et al., J. Med. Chem., 26, 891, (1983)) (0.827 g, 3.3 mMol) by first acetylating the 5'-hydroxyl with acetic anhydride (15 mL) then by brominating the 5 position by the addition of acetic acid (0.5 mL) and bromine (0.566 g). The red-brown solution was stirred at room temperature for two hours. The reaction was taken to an oil in vacuo and triturated with ethyl ether. The oil was dissolved in methanol ammonia to remove the acetyl group. The desired product was isolated by chromatography on silica gel by elution with CHCl3 :MeOH (95:5 v/v). The yield as 32%.

Workup

  1. customtriturated with ethyl ether
  2. dissolutionThe oil was dissolved in methanol ammonia
  3. customto remove the acetyl group

Sources & evidence

ORD record
ord-3355f77f33d24c9d9aba4723a06ffcf6
Source dataset
uspto-grants-1992_09
Patent number
US05145840

Reaction notes

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