483324-01-2

Basic information

• Product Name: 4-(3-Pyridyl)-2-chloropyrimidine
• Synonyms: 2-Chloro-4-pyridin-3-yl-pyrimidine;2-Chloro-4-(3-pyridyl)pyrimidine;4-(3-Pyridyl)-2-chloropyrimidine;PyriMidine, 2-chloro-4-(3-pyridinyl)-;4-(3-pyridyl)-2-chloropyrimidine:2-chloro-4-(3-pyridyl)pyrimidine:
• CAS NO: 483324-01-2
• Molecular Formula: C₉H₆ClN₃
• Molecular Weight: 191.62
• Product Categories: Heterocyclic Building Blocks
• Mol File: 483324-01-2.mol
• Article Data: 19

Chemical Properties

• Boiling Point: 399.5 °C at 760 mmHg
• Flash Point: 227.7 °C
• Appearance: /
• Density: 1.309
• Vapor Pressure: 3.14E-06mmHg at 25°C
• Refractive Index: 1.599
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: 2.34±0.12(Predicted)
• CAS DataBase Reference: 4-(3-Pyridyl)-2-chloropyrimidine(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(3-Pyridyl)-2-chloropyrimidine(483324-01-2)
• EPA Substance Registry System: 4-(3-Pyridyl)-2-chloropyrimidine(483324-01-2)

Safety Data

• Hazardous Substances Data: 483324-01-2(Hazardous Substances Data)

Usage

General Description

4-(3-Pyridyl)-2-chloropyrimidine, also known as 2-Chloro-4-(3-pyridyl)pyrimidine, is a chemical compound with the molecular formula C8H6ClN3. It is a pyrimidine derivative that contains a chloro group and a pyridyl group as its functional groups. This chemical is commonly used as an intermediate in the synthesis of pharmaceuticals and agrochemicals. It is also employed in the development of biologically active compounds, including potential anticancer and antimicrobial agents. Additionally, 4-(3-Pyridyl)-2-chloropyrimidine may be utilized in various research applications in the fields of medicinal and organic chemistry.

InChI:InChI=1/C9H6ClN3/c10-9-12-5-3-8(13-9)7-2-1-4-11-6-7/h1-6H

Upstream product

• 626-55-1 3-Bromopyridine 
• 3934-20-1 2,6-Dichloropyrimidine 
• 1692-25-7 3-pyridylboronic acid 
• 55314-16-4 3-(N,N-dimethylamino)-1-(pyridin-3-yl)prop-2-en-1-one 
• 60573-68-4 3-pyridyllithium 
• 1722-12-9 2-chloropyrimidine 
• 897031-20-8 4-(pyridin-3-yl)-1,2-dihydropyrimidin-2-one 
• 220565-63-9 pyridin-3-ylzinc(II) bromide 

Downstream Products

• 181065-58-7 N-(4-nitrophenyl)-4-(pyridin-3-yl)pyrimidin-2-amine 
• 152460-09-8 N-(5-nitro-2-methylphenyl)-4-(3-pyridinyl)-2-pyrimidineamine 
• 150784-74-0 N-[4-(pyridin-3-yl)pyrimidin-2-yl]benzene-1,4-diamine 
• 1437315-22-4 C₂₂H₁₈N₆O 
• 641569-97-3 4-methyl-3-[[4-(3-pyridyl)-2-pyrimidinyl]amino]benzoic acid ethyl ester 
• 152460-10-1 6-methyl-1-N-(4-(pyridin-3-yl)pyrimidin-2-yl)benzene-1,3-diamine 
• 917392-54-2 methyl 4-methyl-3 -[[4-(pyridin-3-yl)pyrimidin-2-yl]amino]benzoate 
• 641571-10-0 nilotinib 
• 152459-95-5 imatinib 
• 641569-94-0 4-methyl-3-{[4-(pyridin-3-yl)pyrimidin-2-yl]amino}benzoic acid 
• 1352242-48-8 2-methyl-N₁-(4-(pyridin-3-yl)pyrimidin-2-yl)benzene-1,3-diamine 
• 796738-71-1 N-(2-methyl-4-nitrophenyl)-4-(pyridin-3-yl)pyrimidin-2-amine 

Relevant articles and documents

SYNTHESIS OF 6-METHYL-N1-(4-(PYRIDIN-3-YL)PYRIMIDIN-2-YL)BENZENE-1,3-DIAMINE

Processes and useful intermediates for the synthesis of the tyrosine kinase inhibitors Formula (II) nilotinib and Formula (IV) imatinib. Key intermediates, method for their synthesis and their use in a divergent synthesis, making use of a Curtius rearrangement, to nilotinib and imatinib are described.

Investigations into the potential role of metabolites on the anti-leukemic activity of imatinib, nilotinib and midostaurin

The efficacy and side-effects of drugs do not just reflect the biochemical and pharmacodynamic properties of the parent compound, but often comprise of cooperative effects between the properties of the parent and active metabolites. Metabolites of imatinib, nilotinib and midostaurin have been synthesised and evaluated in assays to compare their properties as protein kinase inhibitors with the parent drugs. The N-desmethylmetabolite of imatinib is substantially less active than imatinib as a BCR-ABL1 kinase inhibitor, thus providing an explanation as to why patients producing high levels of this metabolite show a relatively low response rate in chronic myeloid leukaemia (CML) treatment. The hydroxymethylphenyl and N-oxide metabolites of imatinib and nilotinib are only weakly active as BCR-ABL1 inhibitors and are unlikely to play a role in the efficacy of either drug in CML. The 3-(R)-HO-metabolite of midostaurin shows appreciable accumulation following chronic drug administration and, in addition to mutant forms of FLT3, potently inhibits the PDPK1 and VEGFR2 kinases (IC50 values 100 nM), suggesting that it might contribute to drug efficacy in acute myeloid leukaemia patients. The case studies discussed here provide further examples of how the synthesis and characterisation of metabolites can make important contributions to understanding the clinical efficacy of drugs.

Novel 4-(2-pyrimidinylamino)benzamide derivatives as potent hedgehog signaling pathway inhibitors

A series of novel hedgehog signaling pathway inhibitors have been designed and synthesized based on our previously reported scaffold of 4-(2-pyrimidinylamino)benzamide. The Hh signaling pathway inhibitory activities were evaluated by Gli-luciferase reporter method and most compounds showed more potent inhibitory activities than vismodegib. Three compounds were picked out to evaluated in vivo for their PK properties, and compound 23b bearing a 2-pyridyl A-ring and (morpholin-4-yl)methylene at 3-position of D-ring demonstrated satisfactory PK properties. This study suggested the 4-(2-pyrimidinylamino)benzamides were a series of potent Hh signaling pathway inhibitors, deserving to further structural optimization.