Synthesis of deuterium and 15N-labelled 2,5-Bis[5-amidino-2-pyridyl]furan and 2,5-Bis[5-(methoxyamidino)-2-pyridyl]furan

✍ Scribed by Mohamed A. Ismail; David W. Boykin

• Publisher: John Wiley and Sons
• Year: 2006
• Tongue: French
• Weight: 175 KB
• Volume: 49
• Category: Article
• ISSN: 0022-2135
• DOI: 10.1002/jlcr.1111

✦ Synopsis

Abstract

The acetate salt of 2,5‐bis[5‐amidino‐2‐pyridyl]furan‐d~2~/^15^N~2~ (4) was synthesized from 2,5‐bis[5‐cyano‐2‐pyridyl]furan‐d~2~ (2), through the bis‐O‐acetoxyamidoxime followed by hydrogenation. Compound 2 was obtained via a Stille coupling reaction of 6‐chloronicotinonitrile with 2,5‐bis[tri‐n‐butyltin]‐furan‐d~2~ (1). 2,5‐bis[5‐amidino‐2‐pyridyl)furan‐d~6~ (10) was synthesized from 2,5‐bis[5‐cyano‐2‐pyridyl)furan‐d~6~ (9) via a direct reaction with lithium bis(trimethylsilyl)amide, followed by deprotection with ethanolic HCl. ^15^N and/or deuterium‐labelled methoxy‐amidines 5a‐d~2~/^15^N~2~, 5b‐d~8~, 12, 14‐d~6~ were prepared in good yield via direct methylation of their respective diamidoximes with either dimethylsulfate‐d~0~ or dimethylsulfate‐d~6~ in DMF solution and using LiOH as a base. Copyright © 2006 John Wiley & Sons, Ltd.