Aqueous-Phase Suzuki-Miyaura Cross-Coupling Reactions of Free Halopurine Bases

Petr Čapek; Milan Vrábel; Zbyněk Hasník; Radek Pohl; Michal Hocek

doi:10.1055/s-2006-950240

FEATUREARTICLE

Aqueous-Phase Suzuki-Miyaura Cross-Coupling Reactions of Free Halopurine Bases

Petr Čapek, Milan Vrábel, Zbyněk Hasník, Radek Pohl, Michal Hocek*
Gilead & IOCB Research Center, Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, Prague 6, 16610, Czech Republic
Fax: +420(2)20183559; e-Mail: hocek@uochb.cas.cz;

Abstract

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Abstract

The Suzuki-Miyaura reaction of 9-unsubstituted 2-, 6-, and 8-halopurine bases with diverse aryl- and alkenylboronic acids in water-acetonitrile mixtures under microwave irradiation was used for the single-step synthesis of arylpurines. In most cases the product crystallized directly from the reaction mixture in high yields and good purity. The scope and limitations of these reactions were studied.

1 Introduction

2 Results and Discussion

2.1 Cross-Coupling Reactions of 6-Chloro-9H-purine

2.2 Cross-Coupling Reactions of 2-Amino-6-chloro-9H-purine

2.3 Cross-Coupling Reactions of 8-Bromoadenine

2.4 Cross-Coupling Reactions of 2-Chloroadenine

2.5 Cross-Coupling Reactions of 2,6-Dichloro-9H-purine

2.6 NMR Analysis of Arylpurines and Determination of Regioselectivity

3 Conclusions

4 Experimental Section

5 References

Key words

purines - cross-coupling reactions - boronic acids - microwaves - water

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Referenzen

References

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