@Article{IPB-371, author = {Mittersteiner, M. and Pereira, G. S. and Wessjohann, L. A. and Bonacorso, H. G. and Martins, M. A. P. and Zanatta, N.}, title = {{Chemoselective O-alkylation of 4-(trifluoromethyl)pyrimidin-2(1H)-ones using 4-(iodomethyl)pyrimidines}}, year = {2022}, pages = {18930-18939}, journal = {ACS Omega}, doi = {10.1021/acsomega.2c01925}, url = {https://doi.org/10.1021/acsomega.2c01925}, volume = {7}, abstract = {This study reports two strategies for preparing O-alkyl derivatives of 6-substituted-4-(trifluoromethyl)pyrimidin-(1H)-ones: a linear protocol of alkylation,using a CCC-building block followed by [3 + 3]-type cyclocondensation with 2-methylisothiourea sulfate and a convergent protocol based on direct alkylation, using 4-(iodomethyl)-2-(methylthio)-6-(trihalomethyl)pyrimidines. It was found that thecyclocondensation strategy is not feasible; thus, the direct chemoselective O-alkylationwas performed, and 18 derivatives of the targeted pyrimidines were obtained in 70−98%yields. The structure of the products was unambiguously determined via single crystal X-ray analyses and two-dimensional nuclear magnetic resonance experiments.} }