90584-68-2Relevant academic research and scientific papers
Selective Access to Heterocyclic Sulfonamides and Sulfonyl Fluorides via a Parallel Medicinal Chemistry Enabled Method
Tucker, Joseph W.,Chenard, Lois,Young, Joseph M.
, p. 653 - 657 (2015)
A sulfur-functionalized aminoacrolein derivative is used for the efficient and selective synthesis of heterocyclic sulfonyl chlorides, sulfonyl fluorides, and sulfonamides. The development of a 3-step parallel medicinal chemistry (PMC) protocol for the synthesis of pyrazole-4-sulfonamides effectively demonstrates the utility of this reagent. This reactivity was expanded to provide rapid access to other heterocyclic sulfonyl fluorides, including pyrimidines and pyridines, whose corresponding sulfonyl chlorides lack suitable chemical stability.
Lithiation and Thiylation of 5-Bromopyrimidines
Arukwe, Joseph,Keilen, Gunnar,Undheim, Kjell
, p. 530 - 536 (2007/10/02)
5-Thiylated pyrimidines have been prepared by cyclization reactions, and by reactions involving lithiated pyrimidine intermadiates. tert-Butyldimethylsilyl, trimethylsilyl, isopropyl and tert-butyl groups have been tried as O-protecting groups in the lithiation of 5-bromo-2(1H)-pyrimidinone.The trimethylsilyl group is cleaved during lithiation and the tert-butyldimethylsilyl group is cleaved by thiolates generated from disufides during the thiylation. tert-Butyldimethylsilyl chloride together with a base in dichloromethane was used for O-silylation of pyrimidin-2-ones. tert-Butyldimethylsilyl 2-pyrimidinyl ethers are cleaved by acetic acid in chloroform.
