16879-60-0Relevant academic research and scientific papers
Preparation of 5-(Pyrrolylcarbonyl)- and 5-(Imidazolylcarbonyl)-pyrimidines
Gaare, Kristin,Repstad, Terje,Benneche, Tore,Undheim, Kjell
, p. 57 - 62 (2007/10/02)
2-Methylthio-5-(pyrrolylcarbonyl)-pyrimidines have been prepared from 1-methyl-2-tributylstannylpyrrole and 2-methylthiopyrimidine-5-carbonyl chloride by Pd-catalysis.Triphenylarsine was superior to triphenylphosphine as a ligand in the reaction.The reaction with phosphine ligands proceeded well when the polarization of the reactants was reversed as in the reaction between pyrrolecarbonyl chlorides and 2-methylthio-5-tributylstannylpyrimidine. 1-Methyl-5-tributylstannylimidazole has been prepared in a one-pot reaction from 1-methylimidazole in 91percent yield.
Syntheses of 5-Alkenylpyrimidines by Organotin Reactions
Sandosham, Jessie,Benneche, Tore,Moeller, Bjoerg,Undheim, Kjell
, p. 455 - 461 (2007/10/02)
5-Stannylpyrimidines can be prepared from the corresponding bromides by lithiation at -95 deg C and quenching with tributylstannyl chloride.The 5-stannyl-pyrimidine is used in Pd-catalyzed coupling reactions with vinyl bromides.The opposite reaction sequence, i.e.Pd-catalyzed coupling between 5-halopyrimidines and vinyltin derivatives, is also described.Alternatively, the 5-vinylpyrimidines have been obtained by dehydrohalogenation with cesium fluoride and by a modified Wittig reaction. 2-Methylthiopyrimidines are transformed into the 2-methoxy derivatives or 2-pyrimidinones using chloramine-T (CAT) in a simple one-pot synthesis.
