Acetic Acid → 8-Bromo-7H-purine

HRID 722082Notes

Reaction equation

HRID 722082 reaction equation
[N:1]1[CH:9]=[C:8]2[C:4]([N:5]=[CH:6][NH:7]2)=[N:3][CH:2]=1.CC(O)=O.C(O[Na])(C)=O.[Br:19]Br>CO.C1COCC1.C([O-])(=O)C>[Br:19][C:6]1[NH:7][C:8]2[C:4](=[N:3][CH:2]=[N:1][CH:9]=2)[N:5]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 1044PurineHCID 24408BromineHCID 178418247HCID 178418247, compound

Product 1

HCID 218830508-Bromo-7H-purine

Reagents, catalysts & solvents 1

HCID 86598190HCID 86598190, compoundSolvent

Procedure

A solution of purine in MeOH/THF/acetate buffer (1N in each AcOH and AcONa) was treated with Br2 (1.3-equiv. 1M in CHCl3) at room temperature (r.t.) for 16 h. Evaporation, work-up (EtOAc), drying (MgSO4) and flash chromatography afforded the desired 8-bromopurine.

Workup

  1. customEvaporation, work-up (EtOAc)
  2. dry with materialdrying (MgSO4) and flash chromatography

Sources & evidence

ORD record
ord-5bbf77858b6c4cb38cc5ed2a65e278d9
Source dataset
uspto-grants-2006_11
Patent number
US07138401B2

Reaction notes

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