Ammonia → 5-Bromo-2'-deoxyuridine

HRID 1587278Notes

Reaction equation

HRID 1587278 reaction equation
[N:1]([CH:4]([OH:20])[C@H:5]1[O:9][C@@H:8]([N:10]2[CH:17]=[C:16]([Br:18])[C:14](=[O:15])[NH:13][C:11]2=[O:12])[CH2:7][C@@H:6]1[OH:19])=[N+]=[N-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N>N1C=CC=CC=1>[Br:18][C:16]1[C:14](=[O:15])[NH:13][C:11](=[O:12])[N:10]([CH:17]=1)[C@@H:8]1[O:9][C@H:5]([CH2:4][OH:20])[C@@H:6]([OH:19])[CH2:7]1.[NH2:1][CH:4]([OH:20])[C@H:5]1[O:9][C@@H:8]([N:10]2[CH:17]=[C:16]([Br:18])[C:14](=[O:15])[NH:13][C:11]2=[O:12])[CH2:7][C@@H:6]1[OH:19]

Participants

6

Reactant 3

HCID 222AmmoniaHCID 11776TriphenylphosphineHCID 544499215'-Azido-5-bromo-2'-deoxyuridine

Product 2

HCID 60355-Bromo-2'-deoxyuridineHCID 538627455'-Amino-5-bromo-2'-deoxyuridine

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

The 5'-azido derivative of 5-bromo-2'-deoxy uridine is prepared via the method described above. The 5'-azido-5-bromo-2'-deoxyuridine (1 mmol) is treated with triphenyl phosphine (1.5 mmol) in pyridine at room temperature for 2 h. Concentrated ammonia (1 ml) is added to the reaction vessel. After 14 h the solvent is removed under vacuum. The residue is dissolved in THF and this solution is added to hexanes. The precipitate is collected and the solid triturated with the appropriate solvent to afford the 5'-amino-5-bromo-2'-deoxyuridine.

Workup

  1. customAfter 14 h the solvent is removed under vacuum
  2. dissolutionThe residue is dissolved in THF
  3. additionthis solution is added to hexanes
  4. customThe precipitate is collected
  5. customthe solid triturated with the appropriate solvent

Sources & evidence

ORD record
ord-d829be7038bf463ca5d588ce10665c9e
Source dataset
uspto-grants-1993_06
Patent number
US05217866

Reaction notes

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