Oxidative Dehydrosulfurative Cross-Coupling of 3,4-Dihydropyrimidine-2-thiones with Alkynes for Access to 2-Alkynylpyrimidines

Ngoc Son Le Pham; Hyunik Shin; Jun Yong Kang; Jeong-Hun Sohn

doi:10.1021/acs.joc.0c00091

Oxidative Dehydrosulfurative Cross-Coupling of 3,4-Dihydropyrimidine-2-thiones with Alkynes for Access to 2-Alkynylpyrimidines

J Org Chem. 2020 Apr 3;85(7):5087-5096. doi: 10.1021/acs.joc.0c00091. Epub 2020 Mar 16.

Authors

Ngoc Son Le Pham¹, Hyunik Shin², Jun Yong Kang³, Jeong-Hun Sohn¹

Affiliations

¹ Department of Chemistry, Chungnam National University, Daejeon 34134, Republic of Korea.
² Yonsung Fine Chemicals R&D Center, Suwon 16675, Republic of Korea.
³ Department of Chemistry and Biochemistry, University of Nevada, Las Vegas, 4505 South Maryland Parkway, Las Vegas, Nevada 89154-4003, United States.

PMID: 32159960
DOI: 10.1021/acs.joc.0c00091

Abstract

A reaction method is described for the one-step synthesis of 2-alkynylpyrimidines from 3,4-dihydropyrimidin-1H-2-thiones (DHPMs) via dehydrosulfurative Sonogashira cross-coupling with concomitant oxidative dehydrogenation using a Pd/Cu catalytic system. Together with the ready availability of DHPMs possessing various substituents at the C4-C6 positions, this transformation offers rapid and general access to diverse 2-alkynylpyrimidine derivatives.

Publication types

Research Support, Non-U.S. Gov't