13. Purines

  1. John A. Joule1 and
  2. Keith Mills2

Published Online: 6 AUG 2012

DOI: 10.1002/9781118380208.ch13

Heterocyclic Chemistry at a Glance, Second Edition

Heterocyclic Chemistry at a Glance, Second Edition

How to Cite

Joule, J. A. and Mills, K. (2012) Purines, in Heterocyclic Chemistry at a Glance, Second Edition, John Wiley & Sons, Ltd, Chichester, UK. doi: 10.1002/9781118380208.ch13

Author Information

  1. 1

    The School of Chemistry, The University of Manchester, UK

  2. 2

    Independent Consultant, UK

Publication History

  1. Published Online: 6 AUG 2012
  2. Published Print: 4 SEP 2012

ISBN Information

Print ISBN: 9780470971222

Online ISBN: 9781118380208



  • purines;
  • purine reactions, imidazole/pyrimidine ring interplay;
  • nucleoside adenosine, hormone and neurotransmitter;
  • adenosine nucleotides, in energy transfer;
  • electrophilic addition to nitrogen;
  • N-alkylation, similar patterns to protonation;
  • electrophilic substitution at carbon;
  • purines, susceptible to nucleophilic substitution;
  • C-metallated purines by direct deprotonation/halogen–metal exchange;
  • ‘One-step syntheses’


This chapter contains sections titled:

  • Electrophilic addition to nitrogen

  • Electrophilic substitution at carbon

  • N-Deprotonation and N-metallated purines

  • Oxidation

  • Nucleophilic substitution

  • C-Metallated purines by direct deprotonation or halogen–metal exchange

  • Palladium(0)-catalysed reactions

  • Purines with oxygen and amine substituents

  • Ring synthesis – disconnections

  • Synthesis of purines from 4,5-diaminopyrimidines

  • Synthesis of purines from 5-aminoimidazole-4-carboxamide

  • ‘One-step syntheses’

  • Exercises