Synthesis and full characterisation of 6-chloro-2-iodopurine, a template for the functionalisation of purines.

D Taddei; Petr Kilian; Alexandra Martha Zoya Slawin; John Derek Woollins

doi:10.1039/b312629c

Synthesis and full characterisation of 6-chloro-2-iodopurine, a template for the functionalisation of purines.

D Taddei, Petr Kilian, Alexandra Martha Zoya Slawin, John Derek Woollins

Research output: Other contribution

23 Citations (Scopus)

Abstract

A simple and efficient synthesis of 6-chloro-2-iodopurine from hypoxanthine has been achieved. This strategy relied on a regiospecific lithiation/quenching sequence of 6-chloro-9-(tetrahydropyran-2-yl) purine using Harpoon's base and tributyltin chloride. HMBC NMR studies on the product and intermediates confirmed the regioselectivity of this methodology. The molecular structures of the final dihalogenopurine and its 9-protected precursor were determined by single crystal X-ray diffraction.

Original language	English
Volume	2
DOIs	https://doi.org/10.1039/b312629c
Publication status	Published - 2004

Keywords

HUMAN-IMMUNODEFICIENCY-VIRUS
DEPENDENT KINASE INHIBITORS
2,6,9-TRISUBSTITUTED PURINES
ANTIVIRAL ACTIVITY
CDK INHIBITORS
DERIVATIVES
NUCLEOSIDES
LIBRARIES
ADENOSINE
DEOXYNUCLEOSIDES

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

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10.1039/b312629c

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title = "Synthesis and full characterisation of 6-chloro-2-iodopurine, a template for the functionalisation of purines.",

abstract = "A simple and efficient synthesis of 6-chloro-2-iodopurine from hypoxanthine has been achieved. This strategy relied on a regiospecific lithiation/quenching sequence of 6-chloro-9-(tetrahydropyran-2-yl) purine using Harpoon's base and tributyltin chloride. HMBC NMR studies on the product and intermediates confirmed the regioselectivity of this methodology. The molecular structures of the final dihalogenopurine and its 9-protected precursor were determined by single crystal X-ray diffraction.",

keywords = "HUMAN-IMMUNODEFICIENCY-VIRUS, DEPENDENT KINASE INHIBITORS, 2,6,9-TRISUBSTITUTED PURINES, ANTIVIRAL ACTIVITY, CDK INHIBITORS, DERIVATIVES, NUCLEOSIDES, LIBRARIES, ADENOSINE, DEOXYNUCLEOSIDES",

author = "D Taddei and Petr Kilian and Slawin, {Alexandra Martha Zoya} and Woollins, {John Derek}",

note = "Org Biomol Chem",

year = "2004",

doi = "10.1039/b312629c",

language = "English",

volume = "2",

type = "Other",

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TY - GEN

T1 - Synthesis and full characterisation of 6-chloro-2-iodopurine, a template for the functionalisation of purines.

AU - Taddei, D

AU - Kilian, Petr

AU - Slawin, Alexandra Martha Zoya

AU - Woollins, John Derek

N1 - Org Biomol Chem

PY - 2004

Y1 - 2004

N2 - A simple and efficient synthesis of 6-chloro-2-iodopurine from hypoxanthine has been achieved. This strategy relied on a regiospecific lithiation/quenching sequence of 6-chloro-9-(tetrahydropyran-2-yl) purine using Harpoon's base and tributyltin chloride. HMBC NMR studies on the product and intermediates confirmed the regioselectivity of this methodology. The molecular structures of the final dihalogenopurine and its 9-protected precursor were determined by single crystal X-ray diffraction.

AB - A simple and efficient synthesis of 6-chloro-2-iodopurine from hypoxanthine has been achieved. This strategy relied on a regiospecific lithiation/quenching sequence of 6-chloro-9-(tetrahydropyran-2-yl) purine using Harpoon's base and tributyltin chloride. HMBC NMR studies on the product and intermediates confirmed the regioselectivity of this methodology. The molecular structures of the final dihalogenopurine and its 9-protected precursor were determined by single crystal X-ray diffraction.

KW - HUMAN-IMMUNODEFICIENCY-VIRUS

KW - DEPENDENT KINASE INHIBITORS

KW - 2,6,9-TRISUBSTITUTED PURINES

KW - ANTIVIRAL ACTIVITY

KW - CDK INHIBITORS

KW - DERIVATIVES

KW - NUCLEOSIDES

KW - LIBRARIES

KW - ADENOSINE

KW - DEOXYNUCLEOSIDES

UR - http://www.scopus.com/inward/record.url?scp=1642358292&partnerID=8YFLogxK

UR - http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?cmd=Retrieve&db=pubmed&dopt=Abstract&list_uids=14985806

U2 - 10.1039/b312629c

DO - 10.1039/b312629c

M3 - Other contribution

VL - 2

ER -

Synthesis and full characterisation of 6-chloro-2-iodopurine, a template for the functionalisation of purines.

Abstract

Keywords

UN SDGs

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