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Synthesis of 5,6-bis(alkyn-1-yl)pyrimidines and related nucleosides

✍ Scribed by E.Sathyajith Kumarasinghe; Matt A Peterson; Morris J Robins*

Publisher: Elsevier Science
Year: 2000
Tongue: French
Weight: 88 KB
Volume: 41
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(00)01566-5

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✦ Synopsis

Sonogashira coupling of 5-iodo-1-methyluracil or 5%-O-TBDMS-5-iodo-2%,3%-O-isopropylideneuridine with alkynes gave 5-(alkyn-1-yl) derivatives that underwent 6-lithiation/iodination to give 5-(alkyn-1-yl)-6iodo-(1-methyluracil or uridine) intermediates (57-80%). Coupling of the 5-(alkyn-1-yl)-6-iodo intermediates gave 5,6-bis(alkyn-1-yl)pyrimidines and protected nucleosides (51-79%). Two of the 5,6-bis(ethynyl)-1,3-dimethyluracil derivatives underwent Bergman

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