2-Methoxypyrimidine-5-boronic acid

Bezeichnung:2-Methoxypyrimidine-5-boronic acid

CAS-Nr628692-15-9

Englisch Name:2-Methoxypyrimidine-5-boronic acid

CBNumberCB0763158

SummenformelC5H7BN2O3

Molgewicht153.93

MOL-Datei628692-15-9.mol

2-Methoxypyrimidine-5-boronic acid physikalisch-chemischer Eigenschaften

Schmelzpunkt	161°C(lit.)
Siedepunkt	378.3±52.0 °C(Predicted)
Dichte	1.33±0.1 g/cm3(Predicted)
storage temp.	Keep in dark place,Sealed in dry,Room Temperature
Löslichkeit	soluble in Methanol
Aggregatzustand	powder to crystal
pka	5.59±0.11(Predicted)
Farbe	White to Light yellow
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 Datenbank	628692-15-9(CAS DataBase Reference)

Sicherheit

Kennzeichnung gefährlicher	Xi
R-Sätze:	36-41-36/37/38
S-Sätze:	26-39-36/37/39
WGK Germany	WGK 3
HazardClass	IRRITANT
HS Code	29349990
Speicherklasse	11 - Combustible Solids
Hazard Classifications	Acute Tox. 4 Oral Eye Irrit. 2

Gefahreninformationscode (GHS)

2-Methoxypyrimidine-5-boronic acid Chemische Eigenschaften,Einsatz,Produktion Methoden

Chemische Eigenschaften
Off-white to light yellow solid
Verwenden
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].
Vorbereitung Methode
5-Bromo-2-methoxypyrimidine could synthesize 2-Methoxypyrimidine-5-boronic acid as the start material.
Einzelnachweise
[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- d ]pyrimidin-7(6 H )-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

2-Methoxypyrimidine-5-boronic acid Upstream-Materialien And Downstream Produkte

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