321724-19-0

Basic information

• Product Name: Pyrimidine-5-boronic acid pinacol ester
• Synonyms: PYRIMIDIN-5-YLBORONIC ACID PINACOL ESTER;PYRIMIDYL-5-BORONIC ACID PINACOLATE;PYRIMIDYL-5-BORONIC ACID PINACOL ESTER;PYRIMIDINE-5-BORONIC ACID PINACOL ESTER;PINACOL ESTER PYRIMIDINYL-5-BORONIC ACID;PYRIMIDINE-5-BORONIC ACID PINACOLATE;5-Pyrimidineboronic acid pinacol ester;PyriMidine,5-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)-
• CAS NO: 321724-19-0
• Molecular Formula: C₁₀H₁₅BN₂O₂
• Molecular Weight: 206.05
• Product Categories: blocks;BoronicAcids;Heterocycles;Boronic Acid
• Mol File: 321724-19-0.mol
• Article Data: 7

Chemical Properties

• Melting Point: 60-66°C
• Boiling Point: 308.9 °C at 760 mmHg
• Flash Point: 140.6 °C
• Appearance: /
• Density: 1.07 g/cm³
• Vapor Pressure: 0.0012mmHg at 25°C
• Refractive Index: 1.488
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: 1.63±0.10(Predicted)
• CAS DataBase Reference: Pyrimidine-5-boronic acid pinacol ester(CAS DataBase Reference)
• NIST Chemistry Reference: Pyrimidine-5-boronic acid pinacol ester(321724-19-0)
• EPA Substance Registry System: Pyrimidine-5-boronic acid pinacol ester(321724-19-0)

Safety Data

• Hazard Codes: Xi
• HazardClass: IRRITANT
• Hazardous Substances Data: 321724-19-0(Hazardous Substances Data)

Usage

Description

Pyrimidine-5-boronic acid pinacol ester is an organic compound that serves as a key intermediate in the synthesis of various biologically active molecules. It is characterized by its ability to form stable boron-carbon bonds, which makes it a versatile building block in medicinal chemistry and pharmaceutical research.

Uses

Used in Pharmaceutical Industry:
Pyrimidine-5-boronic acid pinacol ester is used as a synthetic intermediate for the preparation of indole derivatives, which are selective inhibitors of all three members of the Pim kinase family. These inhibitors play a crucial role in the development of targeted therapies for various cancers, as Pim kinases are often overexpressed in malignant cells.
Additionally, Pyrimidine-5-boronic acid pinacol ester is used as a key component in the synthesis of inhibitors targeting TGF-β1 and activin A signaling pathways. These pathways are involved in cell proliferation, differentiation, and apoptosis, and their dysregulation has been implicated in numerous diseases, including cancer and fibrosis.

InChI:InChI=1/C10H15BN2O2/c1-9(2)10(3,4)15-11(14-9)8-5-12-7-13-6-8/h5-7H,1-4H3

Upstream product

• 76-09-5 2,3-dimethyl-2,3-butane diol 
• 109299-78-7 pyrimidine 5-boronic acid 
• 4595-59-9 5-bromopyrimidine 
• 73183-34-3 bis(pinacol)diborane 
• 289-95-2 PYRIMIDINE 

Downstream Products

• 174303-53-8 1,4-bis(3,5-pyrimidyl)benzene 
• 1040376-56-4 4-[1-(2,6-dichloro-3-fluoro-phenyl)-ethoxy]-6-pyrimidin-5-yl-pyridazin-3-ylamine 
• 893734-17-3 methyl 4-(pyrimidin-5-yl)benzoate 
• 34771-45-4 5-phenylpyrimidine 
• 2036-41-1 5-methylpyrimidine 

Relevant articles and documents

Preparation method of XPO-1 inhibitor

The invention provides a preparation method of an XPO-1 inhibitor. Specifically, a compound II is prepared from a compound I and pinacol diborate under the action of a Grignard reagent, then the compound II reacts with a compound III under the action of a catalyst and alkali to obtain a compound IV, the compound IV and a compound V are condensed and then hydrolysis is conducted to obtain a compound VI, and finally the final product Eltanexor is prepared through a mixed anhydride method. The preparation method has the advantages of simple and safe synthesis route and operation, easily available raw materials, simple post-treatment and high yield, and is suitable for industrial production.

A Monophosphine Ligand Derived from Anthracene Photodimer: Synthetic Applications for Palladium-Catalyzed Coupling Reactions

Herein, we present an air-stable dianthracenyl monophosphine ligand (diAnthPhos) which can be prepared in two steps from commercially available anthracene derivatives. The ligand exhibits excellent efficiency for palladium-catalyzed coupling reactions. In particular, Miyaura borylation of heterocycle-containing electrophiles can be facilitated employing the diAnthPhos ligand with a broad substrate scope and low catalyst loading. The valuable synthetic utility of the new ligand is further demonstrated by a one-pot Miyaura borylation/Suzuki coupling protocol for heteroaryl-containing substrates.

Mitigation of Acetylcholine Esterase Activity in the 1,7-Diazacarbazole Series of Inhibitors of Checkpoint Kinase 1

Checkpoint kinase 1 (ChK1) plays a key role in the DNA damage response, facilitating cell-cycle arrest to provide sufficient time for lesion repair. This leads to the hypothesis that inhibition of ChK1 might enhance the effectiveness of DNA-damaging therapies in the treatment of cancer. Lead compound 1 (GNE-783), the prototype of the 1,7-diazacarbazole class of ChK1 inhibitors, was found to be a highly potent inhibitor of acetylcholine esterase (AChE) and unsuitable for development. A campaign of analogue synthesis established SAR delineating ChK1 and AChE activities and allowing identification of new leads with improved profiles. In silico docking using a model of AChE permitted rationalization of the observed SAR. Compounds 19 (GNE-900) and 30 (GNE-145) were identified as selective, orally bioavailable ChK1 inhibitors offering excellent in vitro potency with significantly reduced AChE activity. In combination with gemcitabine, these compounds demonstrate an in vivo pharmacodynamic effect and are efficacious in a mouse p53 mutant xenograft model.