5424-21-5

Usage

Uses

Used in Pharmaceutical Synthesis:
2,4-Dichloro-6-methylpyrimidine is used as a key intermediate in the synthesis of (2-chloro-6-methyl-pyrimidin-4-yl)-(2,3-dihydro-benzothiazol-6-yl)-amine, which is an important compound in the development of pharmaceuticals. Its role in this synthesis process is crucial for creating molecules with potential therapeutic applications.
Used in Organic Chemistry:
In the field of organic chemistry, 2,4-Dichloro-6-methylpyrimidine is utilized as a reactant in fluorous synthesis of disubstituted pyrimidines. It reacts with 1H,1H,2H,2H-perfluorodecanethiol, showcasing its versatility in forming diverse chemical structures that can be further explored for various applications, including potential uses in materials science and medicinal chemistry.

InChI:InChI=1/C5H4Cl2N2/c1-3-2-4(6)9-5(7)8-3/h2H,1H3

Upstream product

• 626-48-2 6-Methyluracil 
• 121-44-8 triethylamine 
• 626-48-2 2,4-dihydroxy-6-methylpyrimidine 
• 102-82-9 tributyl-amine 
• 10025-87-3 trichlorophosphate 
• 33238-63-0 5-bromo-6-methyl-2-(methylthio)pyrimidin-4(3H)-one 
• 56-04-2 6-methyl-2-thiouracil 
• 6328-58-1 6-methyl-2-methylsulfanyl-3H-pyrimidin-4-one 
• 15018-56-1 5-bromo-6-methyluracil 
• 121-69-7 N,N-dimethyl-aniline 
• 56745-01-8 5-bromo-2,4-dichloro-6-methylpyrimidine 

Downstream Products

• 62968-34-7 2-chloro-4-methyl-6-piperidinopyrimidine 
• 18247-32-0 2-chloro-4-methyl-6-phenoxypyrimidine 
• 111697-12-2 2,4-bis-(N,N-di-n-propylamino)-6-methylpyrimidine 
• 4871-62-9 6-Methyl-2,4-bis(N-methylanilino)pyrimidine 
• 67914-08-3 2,4-bisethylthio-6-methyl-pyrimidine 
• 696-80-0 2,4-difluoro-6-methyl-pyrimidine 
• 219840-86-5 2-chloro-4-methyl-6-(2-trifluoromethyl-phenyl)-pyrimidine 
• 951231-15-5 2-chloro-4-methyl-6-[4-(trifluoromethyl)phenyl]pyrimidine 

Relevant academic research and scientific papers

Synthesis and structural characterization of the C-6 fluoroalkylated pyrimidine derivatives

C-6 substituted fluoroalkenyl 2,4-dimethoxypyrimidine derivative (4) was synthesized by lithiation of 2,4-dimethoxy-6-methylpyrimidine (3) and subsequent reaction of thus obtained organolithium intermediate with ethyl pentafluoropropionate. The novel 2,4-pyrimidinedione containing 3,3,4,4,4-pentafluoro-1-butenyl side chain (5) was prepared by demethoxylation of 4 using sodium iodide and chlorotrimethylsilane. The structures of 4 and 5 were confirmed by 1H, 13C and 19F NMR spectra, as well as IR spectra. The structure of 4 was also unambiguously confirmed by X-ray crystal structure analysis. The molecules of 4 are weakly linked by aromatic π···π stacking interactions into infinite chains parallel to the a axis.

Novel triazole-sulfonamide bearing pyrimidine moieties with carbonic anhydrase inhibitory action: Design, synthesis, computational and enzyme inhibition studies

A series of new triazole-sulfonamide bearing pyrimidine derivatives were designed and synthesized via click chemistry. All new compounds (SH-1 to SH-28) were validated by 1HNMR, 13CNMR, HRMS, and SH-3 was further structurally validated by X-Ray single diffraction study. These compounds (SH-1 to SH-28) were tested as inhibitors of human carbonic anhydrase (hCA) isoforms, such as hCA I, II, IX and XII, using a stopped flow CO2 hydrase assay. Most of the compounds exhibited significant inhibitory activity against hCA II and weak inhibitory activity against hCA I. The target compounds also displayed moderate to excellent inhibitory activity against tumor-related hCAs IX and XII. Some compounds, e.g., SH-20 (Ki = 9.4 nM), SH-26 (Ki = 1.8 nM) and SH-28 (Ki = 0.82 nM) exhibited excellent inhibitory activity and selectivity profile against hCAs XII over IX. SH-23 displayed promising inhibitory activity and selectivity profile against both tumor-related hCAs IX (Ki = 2.9 nM) as well as XII (Ki = 0.82 nM) over hCA I and II. To understand the molecular interactions, molecular docking study of compounds SH-20, SH-23, SH-26 and SH-28 with hCA XII and SH-23 also with hCA IX were performed. The computational study evidenced favorable interaction between the inhibitors and active residues of both proteins. Some of these derivatives are promising leads for the development of selective, anticancer agents based on CA inhibitors.

Efficient Phosphorus-Free Chlorination of Hydroxy Aza-Arenes and Their Application in One-Pot Pharmaceutical Synthesis

The chlorination of hydroxy aza-arenes with bis(trichloromethyl) carbonate (BTC) and SOCl2 has been effectively performed by refluxing with 5 wt % 4-dimethylaminopyridine (DMAP) as a catalyst. Various substrates are chlorinated with high yields. The obtained chlorinated aza-arenes can be used directly with simple workup for succedent one-pot synthesis on a large scale.

AMINE-SUBSTITUTED HETEROCYCLIC COMPOUNDS AS EHMT2 INHIBITORS, SALTS THEREOF, AND METHODS OF SYNTHESIS THEREOF

The present disclosure relates to amine-substituted heterocyclic compounds. The present disclosure also relates to pharmaceutical compositions containing these compounds and methods of treating a disorder (e.g., cancer) by administering an amine-substituted heterocyclic heterocyclic compound disclosed herein or a pharmaceutical composition thereof to subjects in need thereof. The present disclosure also relates to the use of such compounds for research or other non-therapeutic purposes.

APOPTOSIS INHIBITORS

The invention provides compounds that are inhibitors or covalent modifiers of succinate dehydrogenase subunit B (SDHB) and/or inhibitors of apoptosis, and pharmaceutically acceptable salts, hydrides and stereoisomers thereof. The compounds are employed in pharmaceutical compositions, and methods of making and use, including treating a person in need thereof with an effective amount of the compound or composition.

COMPOUNDS FOR TREATING TUBERCULOSIS

The present invention relates to pyrimidine compounds and compositions for treating tuberculosis. These compounds may be used to target the F1 domain of F-ATP synthase and may be used with bedaquiline or 6-chloro-2-ethyl-N-[[4-[4- [4-(trifluoromethoxy)phenyl]piperidin-1 -yl]phenyl]methyl]imidazo[1,2-a]pyridine-3-carboxamide (Q203) or a combination thereof.

Exploring the potential of newly synthesized 4-methyl-6-morpholino-pyrimidine derivatives as antiproliferative agents

In view of exploring the potential of pyrimidine derivatives as anticancer agents, a series of 4-methyl-6-morpholinopyrimidine derivatives was synthesised and characterised by NMR (1H & 13C), SC-XRD and mass spectral analysis. The in vitro anticancer activity of these compounds was investigated using different human cancer cell lines, namely HeLa (cervix), NCI-H460 (lung), MCF-7 (breast), HepG2 (liver) and IMR-32 (brain). Compounds 4c and 5h exhibited potent anticancer activity in a dose-dependent manner as compared to other derivatives, with IC50 values of 5.88 ± 1.22 and 6.11 ± 2.12 μM on HeLa and NCI-H460, cells respectively. The inhibitory effect of 4c and 5h on cancer cell proliferation was shown to be a consequence of reactive oxygen species (ROS) generation and subsequent induction of cellular apoptosis, as evidenced by an increase in hypodiploid (subG1) population, early apoptotic cell population, caspase-3/7 activity, loss of mitochondrial membrane potential and degradation of nuclear DNA. Furthermore, molecular docking studies revealed that 4c and 5h compounds bind to the ATP binding pocket of the mammalian target of rapamycin (mTOR). Based on our results, we conclude that 4-methyl-6-morpholinopyrimidine derivatives prevent cancer cell proliferation by inducing apoptosis and thus have potential to be further explored for anticancer properties.

COMPOUNDS AND METHODS FOR TREATING TUBERCULOSIS

The present invention relates to compounds of Formula (I), or a pharmaceutically acceptable salt thereof, wherein R1 is selected from methyl, pyrrolidinyl optionally substituted with one or more of fluorine, methyl and hydroxyl, piperidinyl, morpholinyl, fluorobenzylazetidinyl, methylamino substituted with one or more of phenyl, methyl and chlorophenyl, and benzylhydroxylamino; and R2 is selected from phenyl substituted with chlorine or –CHF2, pyridinyl substituted with methyl or –CHF2, -CHF2, cyclopropyl and benzylpyrrolidinyl, to pharmaceutical composition comprising the compounds, to their use in the treatment and or prevention of tuberculosis caused by mycobacterial species, and to their methods of preparation.

ALPHA,BETA-UNSATURATED MONOMERS CAPABLE OF MULTIMERIZATION IN AN AQUEOUS SOLUTION, AND METHODS OF USING SAME

Described herein are monomers capable of forming a biologically useful multimer when in contact with one, two, three or more other monomers in an aqueous media. In one aspect, such monomers may be capable of binding to another monomer in an aqueous media (e.g. in vivo) to form a multimer, (e.g. a dimer). Contemplated monomers may include a ligand moiety, a linker element, and a connector element that joins the ligand moiety and the linker element. In an aqueous media, such contemplated monomers may join together via each linker element and may thus be capable of modulating one or more biomolecules substantially simultaneously, e.g., modulate two or more binding domains on a protein or on different proteins.

Large-scale solvent-free chlorination of hydroxy-pyrimidines,-pyridines,- pyrazines and-amides using equimolar POCl3

Chlorination with equimolar POCl3 can be efficiently achieved not only for hydroxypyrimidines, but also for many other substrates such as 2-hydroxy-pyridines,-quinoxalines, or even-amides. The procedure is solvent-free and involves heating in a sealed reactor at high temperatures using one equivalent of pyridine as base. It is suitable for large scale (multigram) batch preparations.