6299-25-8

Usage

Uses

Used in Organic Synthesis:
4,6-Dichloro-2-(methylthio)pyrimidine is used as a key intermediate in the synthesis of various organic compounds. Its reactivity with (η5-C5H5)Fe(CO)2 allows for the creation of monometallic and bimetallic complexes, which can be further utilized in the development of new molecules with potential applications in various industries.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 4,6-Dichloro-2-(methylthio)pyrimidine is used as a building block for the development of new drugs. Its unique chemical structure and reactivity make it a promising candidate for the synthesis of novel therapeutic agents, particularly those targeting specific biological pathways or receptors.
Used in Chemical Research:
4,6-Dichloro-2-(methylthio)pyrimidine is also employed in chemical research, where it serves as a model compound for studying the properties and behavior of similar molecules. Its ability to form complexes with (η5-C5H5)Fe(CO)2 provides valuable insights into the mechanisms of complex formation and the factors influencing the stability and reactivity of these complexes.
Used in Material Science:
In the field of material science, 4,6-Dichloro-2-(methylthio)pyrimidine can be used to develop new materials with specific properties. The formation of monometallic and bimetallic complexes with (η5-C5H5)Fe(CO)2 can lead to the creation of materials with unique electronic, optical, or magnetic properties, which can be applied in various technological applications.

InChI:InChI=1/C5H4Cl2N2S/c1-2-8-4(6)3(10)5(7)9-2/h10H,1H3

Upstream product

• 1979-98-2 4,6-dihydroxy-2-methylmercaptopyrimidine 
• 29639-68-7 2,4-dihydroxy-2-methylmercaptopyrimidine (keto tautomer) 
• 10026-13-8 phosphorus pentachloride 
• 10025-87-3 trichlorophosphate 
• 77-78-1 dimethyl sulfate 
• 120978-01-0 bis(4,6-dichloropyrimidin-2-yl) disulfide 
• 504-17-6 4,6-dihydroxy-2-mercaptopyrimidine 
• 74-88-4 methyl iodide 

Downstream Products

• 478258-67-2 6-chloro-N-methyl-2-(methylthio)pyrimidin-4-amine 
• 823-09-6 2-(methylsulfanyl)pyrimidine 
• 1005-38-5 4-amino-6-chloro-2-methylthiopyrimidine 
• 91759-35-2 4-chloro-2-(methylthio)-6-<(2,3-dimethylphenyl)oxy>pyrimidine 
• 86626-96-2 (6-Chloro-2-methylsulfanyl-pyrimidin-4-yl)-(2,3-dimethyl-phenyl)-methyl-amine 
• 155670-17-0 6--4-chloro-2-(methylthio)pyrimidine 
• 86626-95-1 6-chloro-N-(2,3-dimethylphenyl)-2-(methylsulfanyl)pyrimidin-4-amine 
• 6632-63-9 6-chloro-2-(methylthio)pyrimidin-4-ol 
• 3289-38-1 4-amino-6-chloro-2-diethylaminopyrimidine 

Relevant academic research and scientific papers

Production process of 4, 6-dimethoxy-2-methylsulfonyl pyrimidine

The invention belongs to the field of organic synthesis, and discloses a production process of 4, 6-dimethoxy-2-methanesulfonyl pyrimidine. According to the production process, dimethyl malonate, thiourea and sodium methoxide are used as raw materials, and cyclization, methylation, chlorination, methoxylation, oxidation and recrystallization are performed to prepare the product. According to the process provided by the invention, the yield of the 4, 6-dimethoxy-2-methylsulfonyl pyrimidine is greater than 90%. Compared with the prior art, methanol, phosphorus oxychloride, methylbenzene and sodium tungstate are repeatedly utilized, so that the wastewater treatment difficulty is reduced, and the production cost is reduced; moreover, sodium sulfate, hydrochloric acid, sodium phosphate and sodium chloride can be co-produced while 4, 6-dimethoxy-2-methylsulfonyl pyrimidine is produced, so that pollutants generated in the production process are greatly reduced, and the economic benefit and environmental benefit of the production process are further improved.

Synthesis of 4,5,6-trichloropyrimidine-2-carbonitrile from 4,6-dichloro-2-(methylthio)pyrimidine

A route to 4,5,6-trichloropyrimidine-2-carbonitrile was developed starting from 4,6-dichloro-2-(methylthio)-pyrimidine. The latter was converted to 4,6-bis(benzyloxy)-5-chloropyrimidine-2-carbonitrile in four steps giving an overall yield of 67%. The steps involved nucleophilic displacement of the 4,6-chlorine atoms by benzyloxide, followed by oxidation of the sulfide group to sulfone, its displacement by cyanide and chlorination at the pyrimidine C5 position with NCS. 4,6-Bis(benzyloxy)-5-chloropyrimidine-2-carbonitrile was finally converted into 4,5,6-trichloropyrimidine-2-carbonitrile in a moderate (30%) yield in a two-step procedure.

Preparation method of 4, 6-dichloro-2-methylthiopyrimidine

The invention provides a preparation method of 4, 6-dichloro-2-methylthiopyrimidine. According to the method, 4,6-dihydroxy-2-methylthiopyrimidine is employed as a raw material and oxalyl chloride isemployed as a chlorination reagent to chlorinate the raw material, and then a reaction is carried out in a solvent to prepare the 4,6-dichloro-2-methylthiopyrimidine. The method has the beneficial effects that the whole technological process is simple, no phosphorus-containing waste liquid or waste solid is generated, the yield is high, the product quality can be stably controlled, and the methodis suitable for industrial production.

Convenient synthesis of 2-(methylsulfonyl)pyrimidine derivatives

An efficient and convenient approach for the preparation of functionalized 2-(methylsulfonyl)pyrimidine derivatives has been developed through cyclic condensation of malonate derivatives with S-methylisothiouronium sulfate followed by derivation and oxidation in water–acetone mixture using oxone as the oxidant. This synthetic strategy provides an efficient and environmentally friendly approach for easy access to 2-(methylsulfonyl)pyrimidine derivatives with considerable yields.

A Strategy for the Triarylation of Pyrrolopyrimidines by Using Microwave-Promoted Cross-Coupling Reactions

New pyrrolo[2,3-d]pyrimidines that have aryl groups at the 2-, 4-, and 6-positions were prepared by the arylation reaction of 4-chloro-7-methyl-2-(methylthio)-6-phenylpyrrolo[2,3-d]pyrimidine (6) and the corresponding arylboronic acid under Suzuki-Miyaura conditions followed by a second arylation under Liebeskind-Srogl cross-coupling conditions. A parallel study that began with the C-2 chemoselective arylation of 6 under Liebeskind-Srogl conditions followed by a Suzuki-Miyaura coupling at C-4 was carried out, and the results of each route were compared. All of the tranformations were performed under microwave irradiation. Several triarylpyrrolopyrimidines were readily prepared from 4,6-dichloro-2-(methylthio)pyrimidine (2) in excellent yields by using effective cross-coupling reactions. An advantage of this method is its tolerance towards various substituted aryl groups.

Studies on the ATP Binding Site of Fyn Kinase for the Identification of New Inhibitors and Their Evaluation as Potential Agents against Tauopathies and Tumors

Fyn is a member of the Src-family of nonreceptor protein-tyrosine kinases. Its abnormal activity has been shown to be related to various human cancers as well as to severe pathologies, such as Alzheimer's and Parkinson's diseases. Herein, a structure-based drug design protocol was employed aimed at identifying novel Fyn inhibitors. Two hits from commercial sources (1, 2) were found active against Fyn with Ki of about 2 μM, while derivative 4a, derived from our internal library, showed a Ki of 0.9 μM. A hit-to-lead optimization effort was then initiated on derivative 4a to improve its potency. Slightly modifications rapidly determine an increase in the binding affinity, with the best inhibitors 4c and 4d having Kis of 70 and 95 nM, respectively. Both compounds were found able to inhibit the phosphorylation of the protein Tau in an Alzheimer's model cell line and showed antiproliferative activities against different cancer cell lines. (Chemical Equation Presented).

Exploring the chemical space around the privileged pyrazolo[3,4-d] pyrimidine scaffold: Toward novel allosteric inhibitors of T315I-mutated Abl

A library of pyrazolo[3,4-d]pyrimidines, endowed with a high level of molecular diversity, has been developed applying a synthetic sequence that allowed C3, N1, C4, and C6 substitution. The enzymatic screening of this "privileged scaffold"-based compound collection, validated the use of a diversity-oriented approach in a field characteristically explored by target-oriented synthesis. In fact, several compounds showed high activity against the selected kinases (i.e., Src, Abl wt, and T315I mutated-form), furthermore and interestingly a new compound has emerged as an allosteric inhibitor of the T315I mutated-form of Abl, opening up new opportunities for the development of a novel class of noncompetitive inhibitors of Abl (T315I).

PROCESSES FOR THE PREPARATION OF BISPYRIBAC SODIUM AND INTERMEDIATES THEREOF

The present disclosure relates to a process for the preparation of Bispyribac-sodium by condensing 2,6-dihydroxy benzoic acid with 2-(alkyl sulfonyl)-4,6-dialkoxy pyrimidine in the presence of at least one base and at least one solvent. The present disclosure also relates to processes for the preparation of 2,6-dihydroxy benzoic acid and 2-(alkyl sulfonyl)-4,6- dialkoxy pyrimidine.

BICYCLIC CARBOXAMIDE INHIBITORS OF KINASES

The present invention relates to compounds of formula (I) or pharmaceutical acceptable salts, wherein X1, X2, X3, X4, R1, R2, R3, A, B, Z, n, and m are defined in the description. The present invention relates also to compositions containing said compounds which are useful for inhibiting kinases such as ALK and methods of treating diseases such as cancer.

SUBSTITUTED PYRAZOLO-PYRIMIDINE COMPOUNDS

The present invention relates to substituted pyrazolo-pyrimidine compounds and methods of synthesizing these compounds. The present invention also relates to pharmaceutical compositions containing substituted pyrazolo-pyrimidine compounds and methods of treating cell proliferative disorders, such as cancer, by administering these compounds or pharmaceutical compositions to subjects in need thereof.