Gilead Sciences, Inc.

Chia-Yun Yu

Dustin S Siegel

Xianghong Wang

Edward Doerffler

Robert William Scott

Bruce Ross

Willard Lew

Lars V Heumann

Andrew W Waltman

Katrien Brak

Andrew C Stevens

Tiago Vieira

Robert Ronald Milburn

Pavel Robertovich Badalov

Sean Timothy Neville

Andrei Chtchemelinine

Mark Charles Whitcomb

Morin Mae Frick

Detian Gao

Clarissa Tadeus

Silvio Campagna

Brittanie Hoang

Lydia Wolfe

Steven Donald Axt

Erik Rueden

Provided are methods of preparing compounds and pharmaceutical compositions comprising a compound Formula VIII for treating Filoviridae virus infections. In one aspect, the compound of Formula VIII is formed from a reaction mixture comprising the compound of Formula IX, the compound of Formula X, a coupling agent such as magnesium chloride and a non-nucleophilic base such as diisopropylethylamine. The compound of Formula IX can be formed from a compound of Formula V and a cyanating agent. The compound of Formula V can be synthesized from a reaction mixture comprising a deprotonating agent such as phenylmagnesium chloride; a silylating agent such as chlorotrimethylsilane; a coupling agent such as isopropylmagnesium chloride, an additive such as LaCl-2LiCl, LaCl, CeCl, NdCl, or YCl; a compound of Formula VI; and 7-iodopyrrolo[2,1-f][1,2,4]triazin-4-amine. The compounds, compositions, and methods provided are particularly useful for the treatment of Marburg virus, Ebola virus and Cueva virus infections.

Methods for the preparation of ribosides

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Edmonton, Canada

Chia-Yun Yu