7377-47-1Relevant academic research and scientific papers
Development of Scalable Synthesis of 5-Butyl-4-(4-methoxyphenyl)-6-phenylpyrimidin-2-amine (WQE-134), a Dual Inhibitor of Nitric Oxide and Prostaglandin E2Production
Baszczyňski, Ond?ej,Dosoudil, Pavel,Havránek, Miroslav,Janeba, Zlatko,Kaiser, Martin Maxmilian,Kolman, Viktor,Kotek, Vladislav
, p. 1718 - 1724 (2020/10/26)
We report a scalable efficient synthesis of 5-butyl-4-(4-methoxyphenyl)-6-phenylpyrimidin-2-amine (WQE-134), a dual inhibitor of nitric oxide and prostaglandin E2 production with potent anti-inflammatory properties. The original five-step synthesis (40% overall yield) was based on two Suzuki-Miyaura reactions and required chromatographic purification of both the intermediate and final products. The novel synthetic pathway is based on cyclization of 2-butyl-1-(4-methoxyphenyl)-3-phenylpropane-1,3-dione with guanidinium methanesulfonate using Eaton's reagent (P2O5/MsOH) at 50 °C. The two-step synthesis (34% overall yield) can be performed on a multigram to kilogram scale, and purification of the final product consists of simple extraction (dichloromethane) and crystallization (ethyl acetate and methanol).
