Deoxyadenosine → 8-Bromo-2'-deoxyadenosine

HRID 895322Notes

Reaction equation

HRID 895322 reaction equation
[C@@H:1]1([N:9]2[C:18]3[N:17]=[CH:16][N:15]=[C:13]([NH2:14])[C:12]=3[N:11]=[CH:10]2)[O:8][C@H:5]([CH2:6][OH:7])[C@@H:3]([OH:4])[CH2:2]1.[Br:19]Br.S(S([O-])=O)([O-])(=O)=O.[Na+].[Na+].[OH-].[Na+]>C([O-])(=O)C.[Na+]>[Br:19][C:10]1[N:9]([C:18]2[N:17]=[CH:16][N:15]=[C:13]([NH2:14])[C:12]=2[N:11]=1)[C@@H:1]1[O:8][C@H:5]([CH2:6][OH:7])[C@@H:3]([OH:4])[CH2:2]1

Participants

6

Reactant 4

HCID 13730DeoxyadenosineHCID 14798Sodium HydroxideHCID 24408BromineHCID 656671Sodium Pyrosulfite

Product 1

HCID 965478-Bromo-2'-deoxyadenosineYield 64%

Reagents, catalysts & solvents 1

HCID 517045Sodium AcetateSolvent

Conditions

Temperature
30 °C

Procedure

2′-deoxyadenosine (7 gm, 25.9 mmol) was dissolved in sodium acetate buffer (150 mL, 1 M, pH 5.0) by worming it to about 50° C., then was cooled dawn to 30° C., then 3 mL of bromine in 100 mL of the same buffer was added drop wise at RT for 15 min, to the reaction. After 6 hrs the TLC on silica gel (20% MeOH in CH2Cl2) showed that all starting material was converted to a new product. The reaction was discolored by adding some sodium metabisulfite (Na2S2O5) while stirring. The color changed to a white solution, and the pH of the reaction was neutralized by adding 1 M NaOH. The reaction mixture was kept at 4° C. (refrigerator) for 16 hrs. The solid material was then filtered, washed with cold water, then acetone to give a solid yellow powder product (5.75 gm, 64%). The structure of this product was confirmed by H-NMR and ES-MS.

Workup

  1. customto about 50° C.
  2. customto the reaction
  3. customwas kept at 4° C.
  4. customfor 16 hrs
  5. filtrationThe solid material was then filtered
  6. washwashed with cold water

Sources & evidence

ORD record
ord-4c999cd990834cd0b7f8ee00b761de84
Source dataset
uspto-grants-2005_07
Patent number
US06916612B2

Reaction notes

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