Solution-phase parallel synthesis of an N-alkylated dihydropteridinone library from fluorous amino acids.
Parallel synthesis of an N-alkylated dihydropteridinone library has been accomplished in five steps starting from two displacement reactions of 4,6-dichloro-5-nitropyrimidine, first with fluorous amino acids, then with secondary amines. The hydrogenation of the nitro group followed by microwave-assisted cyclization gave the dihydropteridinones. Further diversification was achieved by the reaction of dihydropteridinones with benzyl halides to afford mono-N-alkylated products. All the reaction intermediates and final products were purified by SPE or precipitation without the need to perform chromatography.
Nagashima
Tadamichi
T
Fluorous Technologies, Inc, University of Pittsburgh Applied Research Center, 970 William Pitt Way, Pittsburgh, Pennsylvania 15238, USA.
Zhang
Wei
W
D000596:Amino Acids / Q000737:chemistry*; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques / Q000379:methods*; D003500:Cyclization; D005461:Fluorine; D008872:Microwaves; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry; D011621:Pteridines / Q000138:chemical synthesis*
D000596:Amino Acids; D011621:Pteridines; D005461:Fluorine; D010165:Palladium