Effects of Various Bases on Acid-Catalyzed Amination of 2-Chloro-5-ethylpyrimidine: Synthesis of PPARpan Agonist GW693085 was written by Glover, Bobby N.;Jones, Lynda A.;Johnson, Byron S.;Millar, Alan;Osterhout, Martin H.;Xie, Shiping. And the article was included in Journal of Organic Chemistry in 2010.COA of Formula: C11H13NO This article mentions the following:
A unique buffering effect of various bases, i-Pr2NEt and CaCO3 in particular, was observed for the acid-catalyzed chloro displacement of 2-chloro-5-ethylpyrimidine with a 2-methyl-2-phenylpropanamine. The use of the carefully chosen bases was essential for the progression of the chloro displacement as well as the stability of the product in the presence of HCl formed. Research work leading to an efficient synthesis of PPARpan agonist GW693085 (I) is described, featuring highly selective sequential N- and O-alkylations. In the experiment, the researchers used many compounds, for example, 2-(4-Methoxyphenyl)-2-methylpropanenitrile (cas: 5351-07-5COA of Formula: C11H13NO).
2-(4-Methoxyphenyl)-2-methylpropanenitrile (cas: 5351-07-5) belongs to nitriles. Trimerization of aromatic nitriles requires harsh reaction conditions, high temperatures, long reaction times, and pressure. In conventional organic reductions, nitrile is reduced by treatment with lithium aluminium hydride to the amine. Reduction to the imine followed by hydrolysis to the aldehyde takes place in the Stephen aldehyde synthesis, which uses stannous chloride in acid.COA of Formula: C11H13NO
Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts