Reaction of Pyrimidinonethione Derivatives: Synthesis of N‐Methyl‐2‐Hydrizinopyrimidine‐4‐One, Thiazolo[3,4‐b] N‐Methylpyrimidinone; 2‐(1‐Pyrazolonyl) N‐Methylpyrimidine‐4‐one and 2‐Hydrazino‐N‐Methyl Pyrimidine‐4‐One Derivatives

Abstract

6-Aryl-5-cyano-4-pyrimidinone-2-thion derivatives 1a-c reacted with methyl iodide (1:2) to give the corresponding 2-S,N-dimethyl pyrimidine-4-one derivatives 2a-c. Compounds 2a-c were in turn, reacted with hydrazine hydrate to give the sulfur free reaction products 3a-c. These reaction products were taken as the starting materials for the synthesis of several new heterocyclic derivatives. Reaction of 3a-c with acetic anhydride and formic acid gave pyrimido triazines 4a-c and 7a-c, respectively. Their reactions with active methylene containing reagents gave the corresponding 2-(1-pyrazonyl)-N-methyl pyrimidine derivatives 9a-c and 10a-c, respectively. Their reactions with aromatic aldehydes afforded the corresponding 2-hydrazono pyrimidine derivatives 11a-c. The structure of these reactions products were established based on both elemental analysis and spectral data studies.

Design, synthesis and biological evaluation of novel morpholinopyrimidine-5-carbonitrile derivatives as dual PI3K/mTOR inhibitors

“…3. 39 The structure of compound 6 was confirmed through a carbonyl IR band at 1670 cm −1 and the 1 H NMR singlet signal at δ 1.90 ppm assigned to pyrazolidine CH 2 . Imine-enamine tautomerism of compound 6 was emphasized by two deuterium oxide exchangeable singlet signals at δ 9.38 and 9.80 ppm.…”