We report a synthesis of a carbocyclic,
abasic RNA phosphoramidite
decorated with an amino functionality. The building block was efficiently
incorporated into an RNA oligonucleotide in a site-specific manner,
followed by deprotection to a free amino group. The amino moiety could
be further derivatized as exemplified with fluorescein N-hydroxysuccinimide ester. Hence, this convertible building block
may provide access to a variety of RNA oligonucleotides via postsynthetic
amino group functionalization. In particular, providing a vector toward
nucleobase replacements.
The efficient copper-catalyzed construction of imidazopyridinones is described. Beginning from iodopyridinyl ureas, Ullmann coupling provides imidazopyridinones in good yield. Manufacturing by this process is described on 473 kg scale; the scope and limitations of substrates is also detailed.
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