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

HRID 2112397Notes

Reaction equation

HRID 2112397 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>CC(O[Na])=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 (55.8 mmol) 6-amino-9-(2-hydroxyethyl)-9H-purine in 200 ml 0.5M CH3COONa/CH3COOH buffer (pH 4) were added 4 ml of bromine. The reaction mixture was stirred for 8 hours at room temperature. The precipitate was isolated, washed with water and crystallized from ethanol to give 6.13 g (43%) of the desired product.

Workup

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

Sources & evidence

ORD record
ord-47b586e5b39247f9940cec852ec0eead
Source dataset
uspto-grants-2009_04
Patent number
US07524823B2

Reaction notes

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