28230-47-9

Usage

Uses

Used in Organic Synthesis:
(2,6-Dichloro-pyrimidin-4-yl)-phenyl-amine serves as a building block in organic synthesis, playing a crucial role in the creation of various pharmaceuticals, agrochemicals, and materials. Its presence in these syntheses is attributed to its ability to form new carbon-carbon or carbon-nitrogen bonds, which are essential for the development of complex organic molecules.
Used in Pharmaceutical Development:
In the pharmaceutical industry, (2,6-Dichloro-pyrimidin-4-yl)-phenyl-amine is utilized as a key intermediate in the synthesis of new drugs. Its unique structure allows for the design of molecules with specific therapeutic properties, contributing to the advancement of medicine and the treatment of various diseases.
Used in Agrochemical Production:
Similarly, in agrochemicals, (2,6-Dichloro-pyrimidin-4-yl)-phenyl-amine is employed as a starting material for the development of new pesticides, herbicides, and other agricultural chemicals. Its reactivity and structural features enable the creation of effective compounds that can protect crops and enhance agricultural productivity.
Used as a Reagent in Chemical Reactions:
(2,6-Dichloro-pyrimidin-4-yl)-phenyl-amine is also commonly used as a reagent in chemical reactions, particularly for the formation of new carbon-carbon or carbon-nitrogen bonds. This makes it an indispensable tool in the synthesis of a wide range of organic compounds, from simple to complex structures.
Overall, (2,6-Dichloro-pyrimidin-4-yl)-phenyl-amine is a multifaceted compound with applications across various industries, including pharmaceuticals, agrochemicals, and organic synthesis. Its unique properties and potential for use in the development of new drugs and materials underscore its importance in the realm of chemical research and development.

InChI:InChI=1/C10H7Cl2N3/c11-8-6-9(15-10(12)14-8)13-7-4-2-1-3-5-7/h1-6H,(H,13,14,15)

Upstream product

• 3764-01-0 2,4,6-trichloropyrimidine 
• 62-53-3 aniline 
• 74894-28-3 2,5,6-trichloro-4-phenylaminopyrimidine 

Downstream Products

• 1191936-82-9 C₂₂H₂₅N₅O 
• 1350641-01-8 C₂₃H₂₇N₅ 
• 1350641-02-9 C₂₂H₂₂F₃N₅O 
• 1350641-03-0 C₂₂H₂₂F₃N₅O 
• 1350641-04-1 C₂₂H₂₃F₂N₅O 
• 1350641-05-2 C₂₂H₂₃F₂N₅O 
• 1350641-06-3 C₂₃H₂₅N₅O₂ 
• 1350641-07-4 C₂₂H₂₄FN₅O 
• 1637596-26-9 4-chloro-2-(4-methoxybenzyl)amino-6-phenylaminopyrimidine 
• 1637596-24-7 2,4-diisopropoxy-6-phenylaminopyrimidine 
• 90797-75-4 6-chloro-N⁴-phenyl-2,4-pyrimidinediamine 
• 531504-11-7 6-cyclohexylmethoxy-N²,N²-bis-(4-methoxy-benzyl)-N⁴-phenyl-pyrimidine-2,4-diamine 
• 531504-12-8 6-cyclohexylmethoxy-N⁴-phenyl-pyrimidine-2,4-diamine 
• 531504-10-6 6-chloro-N²,N²-bis-(4-methoxy-benzyl)-N⁴-phenyl-pyrimidine-2,4-diamine 

Relevant academic research and scientific papers

Ruthenium-Catalyzed para-Selective C?H Alkylation of Aniline Derivatives

The para-selective C?H alkylation of aniline derivatives furnished with a pyrimidine auxiliary is herein reported. This reaction is proposed to take place via an N?H-activated cyclometalate formed in situ. Experimental and DFT mechanistic studies elucidate a dual role of the ruthenium catalyst. Here the ruthenium catalyst can undergo cyclometalation by N?H metalation (as opposed to C?H metalation in meta-selective processes) and form a redox active ruthenium species, to enable site-selective radical addition at the para position.

Synthesis and structure-activity relationship study of triazine-based inhibitors of the DNA binding of NF-κB

Nuclear transcription factor nuclear factor-kappa B (NF-κB) has diverse pathophysiological functions, and NF-κ B inhibitors are considered to be candidates for multiple therapeutic applications. We previously reported a novel triazine-based NF-κB inhibitor, 2-anilino-4,6-dichloro-1,3,5- triazine (NI241), that directly inhibits DNA binding of NF-κB. Here, we report synthesis of a series of triazine derivatives and evaluation of their structure-activity relationships for NF-κB inhibition. We found that 2-amino-4,6-dichloro-1,3,5-triazine substructure is essential for the inhibitory activity of the lead compound NI241, and modification of NI241 by introduction of an m-methoxy substituent on the phenyl ring afforded the more potent derivative 28. The structure-activity relationships identified in this study suggested a possible mechanism of irreversible NF-κB inhibition by NI241, and should be helpful in the design of other NF-κB inhibitors.

Synthesis and biological evaluation of novel pyrimidine derivatives as sub-micromolar affinity ligands of GalR2

GalR1 and GalR2 represent unique pharmacological targets for treatment of seizures and epilepsy. A novel series of 2,4,6-triaminopyrimidine derivatives were synthesized and found to have sub-micromolar affinity for GalR2. Optimization of a series of 2,4,6

4-Alkoxy-2,6-diaminopyrimidine derivatives: inhibitors of cyclin dependent kinases 1 and 2.

The cyclin dependent kinase (cdk) inhibitor NU6027, 4-cyclohexylmethoxy-5-nitroso-pyrimidine-2,6-diamine (IC(50) vs cdk1/cyclinB1=2.9+/-0.1 microM and IC(50) vs cdk2/cyclinA3=2.2+/-0.6 microM), was used as the basis for the design of a series of 4-alkoxy-2,6-diamino-5-nitrosopyrimidine derivatives. The synthesis and evaluation of 21 compounds as potential inhibitors of cyclin-dependent kinases 1 and 2 is described and the structure-activity relationships relating to NU6027 have been probed. Simple alkoxy- or cycloalkoxy-groups at the O(4)-position were tolerated, with the 4-(2-methylbutoxy)-derivative (IC(50) vs cdk1/cyclinB1=12+/-2 microM and cdk2/cyclinA3=13+/-4 microM) retaining significant activity. Substitutions at the N(6) position were not tolerated. Replacement of the 5-nitroso substituent with ketone, oxime and semicarbazone groups essentially abolished activity. However, the derivative bearing an isosteric 5-formyl group, 2,6-diamino-4-cyclohexylmethoxy-pyrimidine-5-carbaldehyde, showed modest activity (IC(50) vs cdk1/cyclinB1=35+/-3 microM and cdk2/cyclinA3=43+/-3 microM). The X-ray crystal structure of the 5-formyl compound bound to cdk2 has been determined to 2.3A resolution. The intramolecular H-bond deduced from the structure with NU6027 bound to cdk2 is not evident in the structure with the corresponding formyl compound. Thus the parent compound, 4-cyclohexylmethoxy-5-nitrosopyrimidine-2,6-diamine (NU6027), remains the optimal basis for future structure-activity studies for cyclin-dependent kinase inhibitors in this series.

Efficient and regioselective 4-amino-de-chlorination of 2,4,6- trichloropyrimidine with N-sodium carbamates

4-N-Alkoxycarbonyl-2,6-dichloropyrimidines have been synthesized with good to excellent regioselectivity and yields from 2,4,6-trichloropyrimidine and N-sodium carbamates in DMF, at room temperature, in 15-30 minutes. (C) 2000 Elsevier Science Ltd.

2,4,6-Trichloropyrimidine. Reaction with anilines

The reaction of 2,4,6-trichloropyrimidine 1 with a variety of 4-substituted anilines 2 has been investigated. Monosubstitution occurs readily for all anilines except those containing strongly electron-withdrawing groups. The yields of the isomeric product

Polyhalogenoaromatic Compounds. Part 41. Photochemical Dehalogenation and Arylation Reactions of Polyhalogenoaromatic and Polyhalogenoheteroaromatic Compounds

Photolysis of pentachloro- and pentabromo-pyridine in diethyl ether or methanol leads to loss of β-halogen.A product (9) derived from attack on diethyl ether was also identified. 4-Bromotetrachloropyridine also undergoes loss of bromine and tetrachloro-4-iodopyridine loses iodine exclusively.Photodehalogenation of some perhalogenothiophens, tetrachloropyrimidine, and hexachlorobenzene is also described.Photolysis of pentachloroiodobenzene, tetrachloroiodopyridines, and trichloro-5-iodothiophen in benzene gives the corresponding polychloroaryl- or polychloroheteroaryl-benzenes.Photolysis of tetrachloro-4-(phenylthio)pyridine (3) gives 1,3,4-trichlorobenzothienopyridine (6), and the analogous perchloro(phenylthio)pyridine (37) gives the corresponding perchlorobenzothienopyridine (61).The scope of this type of photocyclisation has been explored; starting materials investigated include various arylthiopolyhalogenopyridines, some arylamino- and aryloxy-tetrachloropyridines, and 4-anilinotrichloropyrimidine.