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Synthesis of [8‐ 14 C]‐2,6‐dichloro‐9H‐purine, a radiolabelled precursor for 14 C‐nucleosides
Author(s) -
Valsborg Jacob S.,
Knutsen Lars J. S.,
Lundt Inge,
Foged Christian
Publication year - 1995
Publication title -
journal of labelled compounds and radiopharmaceuticals
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0362-4803
DOI - 10.1002/jlcr.2580360509
Subject(s) - chemistry , carbon 14 , radiochemistry , purine , carbon 13 , chemical synthesis , stereochemistry , organic chemistry , biochemistry , enzyme , nuclear physics , in vitro , physics
Abstract The synthesis of [8‐ 14 C]‐2,6‐dichloro‐9H‐purine ( 2 ), a radiolabelled precursor for preparing 14 C‐labelled nucleosides, is described. Triethyl[ 14 C]orthoformate was reacted with 4,5‐diamino‐2,6‐dichloropyrimidine ( 1 ) in acetonitrile at 90°C with methanesulfonic acid as catalyst to generate 2 in 84% radiochemical yield. Reaction of 2 with 1‐ O ‐acetyl‐2,3,5‐tri‐ O ‐benzoyl‐D‐ribofuranose produced [8‐ 14 C]‐9‐(2,3,5‐tri‐ O ‐benzoyl‐β‐D‐ribofuranosyl)‐2,6‐dichloropurine ( 3 ) in 86% yield. The radiochemical purity of 3 was higher than 98% with a specific activity of 36 mCi/mmol. This method has general application to 14 C‐labelling of purines in drug development.