Influence of remote structure upon regioselectivity in the N-alkylation of 2-amino-6-chloropurine: Application to the synthesis of penciclovir

Article abstract of DOI:10.1080/15257779408011871

Reaction of 2-amino-6-chloropurine with trans-2-alkyl-5-iodoethyl-1,3- dioxanes under basic conditions afforded N-9 and N-7 alkylated products, the product ratio obtained being dependent on the size of the 2-alkyl group. This allowed a highly regioselective key step in the synthesis of the anti-herpes agent penciclovir.

Full text of DOI:10.1080/15257779408011871

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Influence of Remote Structure Upon
Regioselectivity in the N-Alkylation of
2-Amino-6-Chloropurine: Application to
the Synthesis of Penciclovir
Bernadette M. Choudary a , Graham R. Geen a , Trevor J. Grinter a
Fiona S. MacBeath a & Martin J. Parratt a
,
a SmithKline Beecham Pharmaceuticals , Coldharbour Road, The
Pinnacles, Harlow, Essex, CM19 5AD
Published online: 24 Sep 2006.
To cite this article: Bernadette M. Choudary , Graham R. Geen , Trevor J. Grinter , Fiona S. MacBeath
& Martin J. Parratt (1994) Influence of Remote Structure Upon Regioselectivity in the N-Alkylation
of 2-Amino-6-Chloropurine: Application to the Synthesis of Penciclovir, Nucleosides and Nucleotides,
13:4, 979-996, DOI: 10.1080/15257779408011871
To link to this article: http://dx.doi.org/10.1080/15257779408011871
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