Synthesis of N,N-dialkyl-1-(2-alkylthiopyrimidin-4-yl)piperidin- 4-amines as potential heat shock protein inhibitors

Abstract

A new efficient method for synthesizing promising heat shock protein inhibitors, N,N-dialkyl- 1-(2-alkylthiopyrimidin-4-yl)piperidin-4-amines, by the reaction of 2-alkyl-4-chlorothiouracils with 4-(N-alkyl-N-methylamino)piperidines was developed. 2-Alkyl-4-chlorothiouracils were synthesized by alkylation of 2-thiouracil with alkyl iodides and subsequent treatment of the intermediates with POCl₃. 4-(N-Alkyl-N-methylamino)piperidines were prepared by reductive amination of 1-(tert-butoxycarbonyl)-4-piperidinone with methylamine followed by treatment of the intermediate with the appropriate aldehydes.