Synthesis of deuterium and 15N‐labelled 2,5‐Bis[5‐amidino‐2‐pyridyl]furan and 2,5‐Bis[5‐(methoxyamidino)‐2‐pyridyl]furan |
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Abstract: | The acetate salt of 2,5‐bis5‐amidino‐2‐pyridyl]furan‐d2/15N2 ( 4) was synthesized from 2,5‐bis5‐cyano‐2‐pyridyl]furan‐d2 ( 2 ), through the bis‐O‐acetoxyamidoxime followed by hydrogenation. Compound 2 was obtained via a Stille coupling reaction of 6‐chloronicotinonitrile with 2,5‐bistri‐n‐butyltin]‐furan‐d2 ( 1 ). 2,5‐bis5‐amidino‐2‐pyridyl)furan‐d6 ( 10) was synthesized from 2,5‐bis5‐cyano‐2‐pyridyl)furan‐d6 ( 9 ) via a direct reaction with lithium bis(trimethylsilyl)amide, followed by deprotection with ethanolic HCl. 15N and/or deuterium‐labelled methoxy‐amidines 5a ‐d2/15N2, 5b ‐d8, 12 , 14 ‐d6 were prepared in good yield via direct methylation of their respective diamidoximes with either dimethylsulfate‐d0 or dimethylsulfate‐d6 in DMF solution and using LiOH as a base. Copyright © 2006 John Wiley & Sons, Ltd. |
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Keywords: | deuterium‐labelled 15N‐isotopes prodrug bromination Stille coupling |
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