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

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

Uses

Used in Pharmaceutical Industry:
4-(3-Pyridyl)-2-chloropyrimidine is used as an intermediate in the synthesis of pharmaceuticals for its ability to be incorporated into the molecular structures of various drugs. Its unique functional groups allow for the development of biologically active compounds with potential therapeutic applications.
Used in Agrochemical Industry:
In the agrochemical industry, 4-(3-Pyridyl)-2-chloropyrimidine serves as an intermediate in the synthesis of agrochemicals, contributing to the development of effective pesticides and other agricultural products.
Used in Anticancer Research:
4-(3-Pyridyl)-2-chloropyrimidine is used as a potential anticancer agent in research, due to its ability to be modified and incorporated into compounds that target cancer cells. Its unique structure allows for the exploration of its potential in inhibiting the growth and proliferation of cancerous cells.
Used in Antimicrobial Research:
This chemical compound is also utilized in the development of antimicrobial agents, as its structure can be manipulated to target and combat various microorganisms, contributing to the discovery of new antibiotics and antifungal agents.
Used in Medicinal Chemistry Research:
4-(3-Pyridyl)-2-chloropyrimidine is employed in medicinal chemistry research for its potential to be a key component in the synthesis of novel compounds with therapeutic properties. Its functional groups provide a foundation for further chemical modifications and exploration of its biological activity.
Used in Organic Chemistry Research:
In the field of organic chemistry, 4-(3-Pyridyl)-2-chloropyrimidine is used in various research applications, including the study of reaction mechanisms, synthesis techniques, and the development of new organic compounds with potential applications in various industries.

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

Downstream Products

• 112675-67-9 N-(4-methoxyphenyl)-4-(pyridin-3-yl)pyrimidin-2-amine 
• 181065-58-7 N-(4-nitrophenyl)-4-(pyridin-3-yl)pyrimidin-2-amine 
• 611225-84-4 2-nitro-4-(4-(3-pyridyl)pyrimidin-2-yloxy)phenylamine 
• 152460-09-8 N-(5-nitro-2-methylphenyl)-4-(3-pyridinyl)-2-pyrimidineamine 
• 1114991-73-9 4-{[(4-pyridin-3-ylpyrimidin-2-yl)amino]methyl}benzenesulfonamide 
• 1262215-65-5 5-fluoro-6-methyl-N₁-(4-(pyridin-3-yl)pyrimidin-2-yl)benzene-1,3-diamine 
• 1262215-41-7 N-(3-fluoro-4-methyl-5-(4-(pyridin-3-yl)pyrimidin-2-ylamino)phenyl)-4-((4-methylpiperazin-1-yl)methyl)benzamide 
• 1262215-43-9 N-(3-fluoro-4-methyl-5-(4-(pyridin-3-yl)pyrimidin-2-ylamino)phenyl)-4-((4-methylpiperazin-1-yl)methyl)-3-trifluoromethyl-benzamide 
• 1262215-63-3 ethyl N-(3-fluoro-4-methyl-5-(4-(pyridin-3-yl)pyrimidin-2-ylamino)phenyl)carbamate 
• 1433205-40-3 4-(pyridin-3-yl)-N-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzyl)pyrimidin-2-amine,trifluroacetic acid salt 
• 150784-74-0 N-[4-(pyridin-3-yl)pyrimidin-2-yl]benzene-1,4-diamine 
• 1437315-22-4 C₂₂H₁₈N₆O 
• 66521-66-2 4-pyridin-3-ylpyrimidin-2-ylamine 
• 641569-97-3 4-methyl-3-[[4-(3-pyridyl)-2-pyrimidinyl]amino]benzoic acid ethyl ester 

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.

As Hedgehog signal transduction pyrimidine amines and pyridine amine inhibitors

The invention relates to pyrimidinamine and pyridinamine Hedgehog signal conduction inhibitors. The inhibitors are compounds with the structure represented by formula (I) or pharmaceutically acceptable salts thereof. The invention also relates to a medicinal use of the above compounds as hedgehog signal conduction inhibitors.

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.

N-(5-amino-2-methylphenyl)-4-(3-pyridyl)-2-pyrimidineamine derivative with medicine activity, and preparation method thereof

The invention discloses an N-(5-amino-2-methylphenyl)-4-(3-pyridyl)-2-pyrimidineamine derivative with medicine activity, and a preparation method thereof, and belongs to the technical field of medicine synthesis. The structural formula of the N-(5-amino-2-methylphenyl)-4-(3-pyridyl)-2-pyrimidineamine derivative with medicine activity is shown in the description. The invention also discloses a preparation method for the N-(5-amino-2-methylphenyl)-4-(3-pyridyl)-2-pyrimidineamine derivative with anti-cancer activity. The N-(5-amino-2-methylphenyl)-4-(3-pyridyl)-2-pyrimidineamine derivative prepared with the preparation method has good inhibition activity for lung carcinoma cells A549, and has a potential for becoming an anti-tumor medicine.

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.

Introduction of fluorine to phenyl group of 4-(2-pyrimidinylamino)benzamides leading to a series of potent hedgehog signaling pathway inhibitors

In present study, a novel series of fluorine containing 4-(2-pyrimidinylamino)benzamide analogues were designed and synthesized. The hedgehog (Hh) signaling inhibitory activities for these compounds were evaluated by a luciferase reporter method. The preliminary SAR was discussed and many compounds showed potent Hh signaling inhibitory activities. Compound 15h displayed the most potent inhibitory activity, with an IC50 of 0.050?nM. This paper finds the introduction of fluorine to the 4-(2-pyrimidinylamino)benzamide scaffold can lead to a novel series of potent Hh signaling pathway inhibitors.

Synthesis and structure-activity relationship analysis of 5-HT7 receptor antagonists: Piperazin-1-yl substituted unfused heterobiaryls

A series of piperazin-1-yl substituted unfused heterobiaryls was synthesized as ligands of the 5-HT7 receptors. The goal of this project was to elucidate the structural features that affect the 5-HT7 binding affinity of this class of compounds represented by the model ligand 4-(3-furyl)-2-(4-methylpiperazin-1-yl)pyrimidine (2). The SAR studies included systematical structural changes of the pyrimidine core moiety in 2 to quinazoline, pyridine and benzene, changes of the 3-furyl group to other heteroaryl substituents, the presence of various analogs of the 4-methylpiperazin-1-yl group, as well as additional substitutions at positions 5 and 6 of the pyrimidine. Substitution of position 6 of the pyrimidine in the model ligand with an alkyl group results in a substantial increase of the binding affinity (note a change in position numbers due to the nomenclature rules). It was also demonstrated that 4-(3-furyl) moiety is crucial for the 5-HT7 binding affinity of the substituted pyrimidines, although, the pyrimidine core can be replaced with a pyridine ring without a dramatic loss of the binding affinity. The selected ethylpyrimidine (12) and butylpyrimidine (13) analogs of high 5-HT7 binding affinity showed antagonistic properties in cAMP functional test and varied selectivity profile-compound 12 can be regarded as a dual 5-HT7 /5-HT2A R ligand, and 13 as a multi-receptor (5-HT7 , 5-HT2A , 5-HT6 and D2 ) agent.

Imatinib preparation method

The invention relates to the technical field of medicine, and in particular, relates to a synthetic process of an anti-tumor medicine. The invention aims to provide an imatinib preparation method which has the advantages of simple operation, easily obtained raw materials, short reaction steps, high yield and environmental friendliness. In the imatinib preparation method, formation of a pyrimidine ring abandons a cyanamide method having relatively great toxicity and a phosphorus oxychloride method having strong corrosion, and by a Suzuki reaction between 2,4-dichloropyrimidine and 3-boric acid pyridine, a key intermediate 2-chloro-4-(3-pyridyl)pyrimidine is rapidly obtained through a one-step method; with use of a characteristic that a 2-site of 2-chloro-4-(3-pyridyl)pyrimidine is easily attacked by a nucleophilic reagent, imatinib is prepared with relatively high conversion rate through a nucleophilic substitution reaction; a metal catalysis method and other methods which are not easy to industrialize and are used in many literatures are discarded. The synthetic process has the advantages of easily obtained raw materials, short reaction steps, high yield and environmental friendliness.

Preparing method for 4-methyl-3-[[4-(3-pyridyl)-2-pyrimidyl]amidogen]ethyl benzoate

The invention relates to a preparing method for 4-methyl-3-[[4-(3-pyridyl)-2-pyrimidyl]amidogen]ethyl benzoate and belongs to the technical field of compound synthesis. The preparing method comprises the following steps of using triacetyl pyridine as a beginning raw material, condensing a product generated after urea loop closing and carbonyl chloro substitution with 3-amino-4-methyl ethyl benzoate to generate a key intermediate (I). Compared with an existing synthetic method, the preparing method is moderate in reacting condition and high in yield and has practical value. In addition, the raw material of the preparing method is cheap, easy to obtain and low in price. A synthetic route of the preparing method is as follow in the specification.

BENZIMIDAZOLE DERIVATIVES AS SELECTIVE PROTEINE KINASE INHIBITORS

The present invention relates to compounds of formula (I) or pharmaceutically acceptable salts thereof. Wherein n, R1, R2, R3, R4, R5, A, Q and X are as defined in the description. These compounds selectively modulate, regulate, and/or inhibit signal transduction mediated by certain native and/or mutant proteine kinases implicated in a variety of human and animal diseases such as cell proliferative, metabolic, allergic, and degenerative disorders. More particularly, these compounds are potent and selective native and/or mutant c-kit inhibitors.