Literature DB >> 22368305

One-pot Double Suzuki Couplings of Dichloropyrimidines.

Samantha C Anderson, Scott T Handy.   

Abstract

An effective one-pot, regioselective double Suzuki coupling of 2,4-dichloropyrimidine has been developed, which enables the quick and efficient synthesis of diarylated pyrimidines. The choice of solvent proved critical to the success of this reaction sequence, with alcoholic solvent mixtures affording much greater reactivity and correspondingly lower temperatures than the use of polar aprotic solvents.

Entities:  

Year:  2010        PMID: 22368305      PMCID: PMC3285113          DOI: 10.1055/s-0030-1258150

Source DB:  PubMed          Journal:  Synthesis (Stuttg)        ISSN: 0039-7881            Impact factor:   3.157


  13 in total

1.  Imidazo[1,2-a]pyrimidines as functionally selective GABA(A) ligands.

Authors:  Wesley P Blackaby; John R Atack; Frances Bromidge; José L Castro; Simon C Goodacre; David J Hallett; Richard T Lewis; George R Marshall; Andrew Pike; Alison J Smith; Leslie J Street; David F D Tattersall; Keith A Wafford
Journal:  Bioorg Med Chem Lett       Date:  2006-01-06       Impact factor: 2.823

2.  A simple guide for predicting regioselectivity in the coupling of polyhaloheteroaromatics.

Authors:  Scott T Handy; Yanan Zhang
Journal:  Chem Commun (Camb)       Date:  2005-11-21       Impact factor: 6.222

3.  Arylation of halogenated pyrimidines via a Suzuki coupling reaction.

Authors:  J M Schomaker; T J Delia
Journal:  J Org Chem       Date:  2001-10-19       Impact factor: 4.354

4.  4-Aryl-2-anilinopyrimidines as corticotropin-releasing hormone (CRH) antagonists.

Authors:  A J Cocuzza; F W Hobbs; C R Arnold; D R Chidester; J A Yarem; S Culp; L Fitzgerald; P J Gilligan
Journal:  Bioorg Med Chem Lett       Date:  1999-04-05       Impact factor: 2.823

5.  Regioselective dicouplings: application to differentially substituted pyrroles.

Authors:  Scott T Handy; Jesse J Sabatini
Journal:  Org Lett       Date:  2006-04-13       Impact factor: 6.005

6.  Synthesis, SAR, and antitumor properties of diamino-C,N-diarylpyrimidine positional isomers: inhibitors of lysophosphatidic acid acyltransferase-beta.

Authors:  Baoqing Gong; Feng Hong; Cory Kohm; Scott Jenkins; John Tulinsky; Rama Bhatt; Peter De Vries; Jack W Singer; Peter Klein
Journal:  Bioorg Med Chem Lett       Date:  2004-05-03       Impact factor: 2.823

7.  Disubstituted pyridines: the double-coupling approach.

Authors:  Scott T Handy; Thomas Wilson; Aaron Muth
Journal:  J Org Chem       Date:  2007-10-05       Impact factor: 4.354

8.  Facile assembly of fused benzo[4,5]furo heterocycles.

Authors:  Jing Liu; Anne E Fitzgerald; Neelakandha S Mani
Journal:  J Org Chem       Date:  2008-03-11       Impact factor: 4.354

9.  Pyrimidine-based inhibitors of CaMKIIdelta.

Authors:  Babu Mavunkel; Yong-Jin Xu; Bindu Goyal; Don Lim; Qing Lu; Zheng Chen; Dan-Xiong Wang; Jeffrey Higaki; Indrani Chakraborty; Albert Liclican; Steve Sideris; Maureen Laney; Ulrike Delling; Rosanne Catalano; Linda S Higgins; Hui Wang; Jing Wang; Ying Feng; Sundeep Dugar; Daniel E Levy
Journal:  Bioorg Med Chem Lett       Date:  2008-03-04       Impact factor: 2.823

10.  Trisubstituted pyrimidines as transient receptor potential vanilloid 1 (TRPV1) antagonists with improved solubility.

Authors:  Xianghong Wang; Partha P Chakrabarti; Vassil I Ognyanov; Liping H Pettus; Rami Tamir; Helming Tan; Phi Tang; James J S Treanor; Narender R Gavva; Mark H Norman
Journal:  Bioorg Med Chem Lett       Date:  2007-10-15       Impact factor: 2.823

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  2 in total

1.  Site-selective Suzuki-Miyaura coupling of heteroaryl halides - understanding the trends for pharmaceutically important classes.

Authors:  Joshua Almond-Thynne; David C Blakemore; David C Pryde; Alan C Spivey
Journal:  Chem Sci       Date:  2016-08-09       Impact factor: 9.825

2.  Carbazole- and Triphenylamine-Substituted Pyrimidines: Synthesis and Photophysical Properties.

Authors:  Sylvain Achelle; Julián Rodríguez-López; Massinissa Larbani; Rodrigo Plaza-Pedroche; Françoise Robin-le Guen
Journal:  Molecules       Date:  2019-05-05       Impact factor: 4.411

  2 in total

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