A concise route to MK-4482 (EIDD-2801) from cytidine

N. Vasudevan; Grace P. Ahlqvist; Catherine P. McGeough; Dinesh J. Paymode; Flavio S. P. Cardoso; Tobias Lucas; Jule-Phillip Dietz; Till Opatz; Timothy F. Jamison; Frank B. Gupton; David R. Snead

doi:10.1039/D0CC05944G

A concise route to MK-4482 (EIDD-2801) from cytidine†

N. Vasudevan,^a Grace P. Ahlqvist,

^b Catherine P. McGeough,^b Dinesh J. Paymode,^a Flavio S. P. Cardoso,

^a Tobias Lucas,^c Jule-Phillip Dietz,^c Till Opatz,

^c Timothy F. Jamison,

^b Frank B. Gupton^a and David R. Snead

*^a

Author affiliations

* Corresponding authors

^a Medicines for All Institute, 737 N. 5th St., Box 980100, Richmond, VA, USA
E-mail: drsnead@vcu.edu

^b Department of Chemistry, Massachusetts Institute of Technology, 77 Massachusetts Ave, Cambridge, Massachusetts, USA

^c Department of Chemistry, Johannes Gutenberg University, Duesbergweg 10-14, Mainz 55128, Germany

Abstract

A two-step route to MK-4482 (EIDD-2801, 1) was developed consisting of an esterification and hydroxamination of cytidine. The selective acylation and direct amination eliminate the need for protecting and activating groups and proceed in overall yield of 75%, a significant advancement over the reported yield of 17%. The step count is reduced from five transformations to two, and expensive uridine is replaced with the more available cytidine.

Chemical Communications

A concise route to MK-4482 (EIDD-2801) from cytidine†

Abstract

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A concise route to MK-4482 (EIDD-2801) from cytidine

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