36315-02-3Relevant academic research and scientific papers
A phase-switch purification approach for the expedient removal of tagged reagents and scavengers following their application in organic synthesis
Siu, Jason,Baxendale, Ian R.,Lewthwaite, Russell A.,Ley, Steven V.
, p. 3140 - 3160 (2007/10/03)
In this paper we wish to report on a variety of expedient chemical transformations and purifications achieved via a generic 'catch and release' methodology, based on a synthetically inert bipyridyl chelating tag that can be selectively captured with a resin-bound copper(II) species. Utilising this approach we are able to derive many of the same benefits associated with both solid phase synthesis and supported reagent methods. The Royal Society of Chemistry 2005.
Structural studies on bioactive compounds. Part 29: Palladium catalysed arylations and alkynylations of sterically hindered immunomodulatory 2-amino- 5-halo-4,6-(disubstituted)pyrimidines
Hannah, Duncan R.,Sherer, Edward C.,Davies, Roy V.,Titman, Roger B.,Laughton, Charles A.,Stevens, Malcolm F. G.
, p. 739 - 750 (2007/10/03)
The immunological agent bropirimine 5 is a tetra-substituted pyrimidine with anticancer and interferon-inducing properties. Synthetic routes to novel 5-aryl analogues of bropirimine have been developed and their potential molecular recognition properties analysed by molecular modelling methods. Sterically challenged 2-amino-5-halo-6-phenylpyrimidin-4-ones (halo=Br or I) are poor substrates for palladium catalysed Suzuki cross-coupling reactions with benzeneboronic acid because the basic conditions of the reaction converts the amphoteric pyrimidinones to their unreactive enolic forms. Palladium-mediated reductive dehalogenation of the pyrimidinone substrates effectively competes with cross-coupling. 2-Amino-5-halo-4-methoxy-6- phenylpyrimidines can be converted to a range of 5-aryl derivatives with the 5-iodopyrimidines being the most efficient substrates. Hydrolysis of the 2- amino-5-aryl-4-methoxy-6-phenylpyrimidines affords the required pyrimidin-4- ones in high yields. Semi-empirical quantum mechanical calculations show how the nature of the 5-substituent influences the equilibrium between the 1H- and 3H-tautomeric forms, and the rotational freedom about the bond connecting the 6-phenyl group and the pyrimidine ring. Both of these factors may influence the biological properties of these compounds. (C) 2000 Elsevier Science Ltd.
