molbank Short Note Ethyl 6-Methyl-2-oxo-4-{4-[(1-phenyl-1H -1,2,3-triazol- 4-yl)methoxy]phenyl}-1,2,3,4-tetrahydropyrimidine- 5-carboxylate Itamar Luís Gonçalves 1 , Gabriel Oliveira de Azambuja 1 , Leonardo Davi 1 , Guilherme Arraché Gonçalves 1 , Luciano Porto Kagami 1 , Gustavo Machado das Neves 1 , João Pedro Silveira 1 ,Rômulo Faria Santos Canto 1,2 and Vera Lucia Eifler-Lima 1, * 1 Laboratório de Síntese Orgânica Medicinal (LaSOM®), Faculty of Pharmaceutical Sciences, Federal University of Rio Grande do Sul, Ipiranga Avenue, 2752 Porto Alegre, RS, Brazil 2 Laboratório de Química Medicinal de Compostos de Selênio (QMCSe), Federal University of Health Sciences of Porto Alegre, Sarmento Leite Street, 245 Porto Alegre, RS, Brazil * Correspondence: veraeifler@ufrgs.br; Tel.: +55-51-3308-5362 Received: 2 July 2019; Accepted: 1 August 2019; Published: 14 August 2019   Abstract: The Biginelli reaction is an acid-catalyzed, three-component reaction between an aldehyde, a hydrogen methylene active compound, and urea (or its analogue) and constitutes a rapid and easy synthesis of highly functionalized heterocycles. Synthesis of ethyl 6-methyl-2-oxo-4-{4-[(1-phenyl- 1H-1,2,3-triazol-4-yl)methoxy]phenyl}-1,2,3,4-tetrahydropyrimidine-5-carboxylate, identified by our laboratory code LaSOM ® 293, was achieved using the Biginelli reaction as the key step, followed by the Huisgen 1,3-dipolar cycloaddition in a convergent four-step route. The product LaSOM ® 293 was obtained with a yield of 84%. Keywords: Biginelli reaction; 3,4-dihydropyrimidinone; triazole; LaSOM ® 293 1. Introduction The synthesis of 3,4-dihydropyrimidinones (DHPMs) was reported by the Italian chemist Pietro Biginelli, in 1893, using the one-pot multicomponent reaction of benzaldehyde, urea, and ethyl acetoacetate and employing hydrochloric acid as the catalyst [1]. In recent decades, important advances in this field have been reported, allowing for the structural diversification of this heterocycle class. The structural diversity of this reaction renders it a powerful tool using very simple building blocks [2]. Furthermore, the pharmacological effect of DHPMs has been widely investigated, mainly focusing on anticancer drug development [3]. Monastrol is a DHPM identified as a kinesin-5 inhibitor, involved in the separation of genetic material during mitosis. The inhibition of this enzyme leads to cell cycle arrest at the G 2 /M phase and activation of signaling ways, which leads to cellular apoptosis [4]. Recent investigations have reported that the monastrol derivatives with an aromatic ring at N1 position showed improved activity against rat and human glioma cell lines [5]. Triazole is another important scaffold in medicinal chemistry. This is due to its ability to interact with a wide number of receptors in biological systems through different non-covalent interactions, and thus exhibit versatile pharmacological profiles [6,7]. Another relevant aspect of 1,2,3-triazole is the ease with which it can be obtained from an azide and an alkyne using the Huisgen 1,3-dipolar cycloaddition [8]. Hybrid compounds have recently gained increased attention, combining parts of two pharmacophores in a single molecule [9]. The current study reports a four-step synthesis of the highly functionalized hybrid DHPM-triazole LaSOM ® 293. This is part of an investigation to identify novel compounds with anticancer properties using the Biginelli reaction followed by 1,3-dipolar cycloaddition. Molbank 2019, 2019, M1076; doi:10.3390/M1076 www.mdpi.com/journal/molbank