Efficient assembly of 2,5,6-substituted pyrimidines via MgI(2)-mediated Morita-Baylis-Hillman reaction.
A mild and efficient protocol for the synthesis of a 2,6-disubstituted pyrimidine-5-carboxylate library via a Morita-Baylis-Hillman (MBH) adduct is described. Herein, the three step methodology involves the use of substituted alpha-iodomethylene beta-keto ester intermediates obtained after oxidation of the MBH adducts, which are condensed with various types of amidine or guanidine derivatives, to generate the 2, 6-disubstituted pyrimidines-5-carboxylate libraries.
Sharma
Vasudha
V
Drug Discovery Department, H. Lee Moffitt Cancer Center, 12902 Magnolia Dr., MRC 4E, Tampa, FL 33612, USA.
McLaughlin
Mark L
ML
D002264:Carboxylic Acids / Q000737:chemistry; D020650:Combinatorial Chemistry Techniques / Q000379:methods*; D004952:Esters / Q000737:chemistry; D006847:Hydrocarbons, Iodinated / Q000737:chemistry; D007454:Iodides / Q000737:chemistry*; D017616:Magnesium Compounds / Q000737:chemistry*; D008956:Models, Chemical; D010084:Oxidation-Reduction; D011743:Pyrimidines / Q000138:chemical synthesis* / Q000737:chemistry
D002264:Carboxylic Acids; D004952:Esters; D006847:Hydrocarbons, Iodinated; D007454:Iodides; D017616:Magnesium Compounds; D011743:Pyrimidines; C027946:methylene iodide; C510205:magnesium iodide