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Synthesis of [8-14C]-2,6-dichloro-9H-purine, a radiolabelled precursor for 14C-nucleosides

✍ Scribed by Jacob S. Valsborg; Lars J. S. Knutsen; Inge Lundt; Christian Foged

Publisher: John Wiley and Sons
Year: 1995
Tongue: French
Weight: 321 KB
Volume: 36
Category: Article
ISSN: 0022-2135
DOI: 10.1002/jlcr.2580360509

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✦ Synopsis

The synthesis of [8-'4C]-2,6-dichloro-9H-purine (z), a radiolabelled precursor for preparing ''C-labelled nucleosides, is described. Triethyl ['4C]orthoformate was reacted with 4,5-diamino-2,6-dichloropyrimidine (1) in acetonitrile at 90°C with methanesutfonic acid as catalyst to generate 2 in 84% radiochemical yield. Reaction of 2. with 1-0acetyl-2,3,5-tri-O-benzoyl-D-ribofuranose produced [8-'4C]-9-(2,3,5-tri-O-benzoyl-P-D-ribofuranosyl)-2,6-dichloropurine (3) in 86% yield. The radiochemical purity of 3 was higher than 98% with a specific activity of 36 mCilmmol. This method has general application to 14C-labelling of purines in drug development.

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