Bromine → 2-(6-amino-8-bromo-9H-purin-9-yl)ethanol

HRID 1920653Notes

Reaction equation

HRID 1920653 reaction equation
[NH2:1][C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][N:6]2[CH2:11][CH2:12][OH:13].[Br:14]Br>C(O[Na])(C)=O.CC(O)=O>[NH2:1][C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[N:4]=[C:5]([Br:14])[N:6]2[CH2:11][CH2:12][OH:13]

Participants

4

Reactant 2

HCID 24408BromineHCID 2426522-(6-Aminopurin-9-yl)ethanol

Product 1

HCID 445724692-(6-amino-8-bromo-9H-purin-9-yl)ethanolYield 43%

Reagents, catalysts & solvents 1

HCID 178476574sodium;acetic acid;acetateSolvent

Procedure

To a solution of 10 g 2-(6-amino-purin-9-yl)ethanol in 200 ml 0.5M AcONa/AcOH buffer pH 4 were added 4 ml of Br2. The resulting mixture was stirred at room temperature for 8 hours. The precipitated product was isolated, washed with water and crystallized from ethanol to give 6.13 g (43%) of the desired compound.

Workup

  1. customThe precipitated product was isolated
  2. washwashed with water
  3. customcrystallized from ethanol

Sources & evidence

ORD record
ord-7c2c581a412e4451ae310470494ed016
Source dataset
uspto-grants-2012_05
Patent number
US08173609B2

Reaction notes

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