628692-15-9

Off-white to light yellow solid

2-Methoxypyrimidine-5-boronic acid serves as a coupling partner in Suzuki–Miyaura reactions to synthesize diverse heterocyclic scaffolds. It reacts with intermediates such as compound 26 or 6-bromo-3-(4-hydroxyphenyl)-coumarin using potassium carbonate and palladium catalysts (e.g., Pd(OAc)₂ or 1,1′-bis(di-tert-butylphosphino)ferrocene palladium dichloride) in solvents including DMF or deep eutectic systems at 85 °C. The reagent also couples with 2-(4-((4-chloro-6-morpholino-1,3,5-triazin-2-yl)amino)phenyl)ethan-1-ol in DME/aqueous sodium carbonate under microwave heating[1][2][3]. The compound participates in Liebeskind–Srögl couplings with thioester or amide intermediates (such as series 18a–18c or 20a–20f) using tetrakis(triphenylphosphine)palladium(0) and copper(I) thiophene-2-carboxylate in THF at 100 °C, yielding target products in ranges of 22–55% or 29–50%[1].

5-Bromo-2-methoxypyrimidine could synthesize 2-Methoxypyrimidine-5-boronic acid as the start material.

[1]Wang, H., Liao, W., Li, Y., Guo, A., Liu, Z., Guo, X., Wang, K., Zheng, Y., Wang, Z., Wang, W., Wang, X., Zhang, L., Sun, Q., & Huang, Z. (2026). Discovery of Novel Thiazolo[4,5- <i>d</i> ]pyrimidin-7(6 <i>H</i> )-Ones as Extrasynaptic δ-GABA _A Receptor-Preferring PAMs with Rapid Antidepressant-like Efficacy. Journal of Medicinal Chemistry, 69(14), 16476–16508. https://doi.org/10.1021/acs.jmedchem.5c03830
[2]Nelson, R. A., Jr., Schronce, T., Huang, Y., Albugami, A., Kulik, G., & Welker, M. E. (2018). Synthesis and PI 3-Kinase Inhibition Activity of Some Novel 2,4,6-Trisubstituted 1,3,5-Triazines. Molecules, 23(7), 1628. https://doi.org/10.3390/molecules23071628
[3]Katopodi, A., Nikolaou, N., Kakokefalou, V., Alexandratou, E., Matzapetakis, M., Zervou, M., & Detsi, A. (2024). A Ligand-Free Approach towards Coumarin Analogs via Natural Deep Eutectic Solvent-Mediated Suzuki–Miyaura Coupling. Molecules, 29(18), 4398. https://doi.org/10.3390/molecules29184398