| Identification | More | [Name]
2-Methoxypyrimidine-5-boronic acid | [CAS]
628692-15-9 | [Synonyms]
2-METHOXY-5-PYRIMIDINEBORONIC ACID
2-METHOXYPYRIMIDIN-5-YLBORONIC ACID
2-METHOXYPYRIMIDINE-5-BORONIC ACID
2-METHOXYL-5-PYRIMIDYLBORIC ACID
2-Methoxypyrimidine-5-boronic acid ,98% | [EINECS(EC#)]
670-240-4 | [Molecular Formula]
C5H7BN2O3 | [MDL Number]
MFCD03094664 | [Molecular Weight]
153.93 | [MOL File]
628692-15-9.mol |
| Chemical Properties | Back Directory | [Melting point ]
161°C(lit.) | [Boiling point ]
378.3±52.0 °C(Predicted) | [density ]
1.33±0.1 g/cm3(Predicted) | [storage temp. ]
Keep in dark place,Sealed in dry,Room Temperature | [solubility ]
soluble in Methanol | [form ]
powder to crystal | [pka]
5.59±0.11(Predicted) | [color ]
White to Light yellow | [Detection Methods]
HPLC,NMR | [InChI]
InChI=1S/C5H7BN2O3/c1-11-5-7-2-4(3-8-5)6(9)10/h2-3,9-10H,1H3 | [InChIKey]
YPWAJLGHACDYQS-UHFFFAOYSA-N | [SMILES]
B(C1=CN=C(OC)N=C1)(O)O | [CAS DataBase Reference]
628692-15-9(CAS DataBase Reference) |
| Hazard Information | Back Directory | [Chemical Properties]
Off-white to light yellow solid | [Uses]
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]. | [Production Methods]
5-Bromo-2-methoxypyrimidine could synthesize 2-Methoxypyrimidine-5-boronic acid as the start material. | [References]
[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 <sub>A</sub> 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 |
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