cas 6299-25-8, 4,6-Dichloro-2-(methylthio)pyrimidine

Articles about 6299-25-8Total 16 be found

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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.
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Paragraph 0014; 0016; 0020; 0022; 0024

(2021/03/30)

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.
Kalogirou, Andreas S.,Koutentis, Panayiotis A.
(2020/09/07)

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.
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Paragraph 0029-0040

(2019/07/04)

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.
Huang, Tong-Hui,Zhou, Shan-Shan,Wu, Xin,An, Lin,Yin, Xiao-Xing
supporting information
p. 714 - 720
(2018/02/16)

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.
Prieur, Vanessa,Pujol, M. Dolors,Guillaumet, Gérald
supporting information
p. 6547 - 6556
(2015/10/19)

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).
Tintori, Cristina,La Sala, Giuseppina,Vignaroli, Giulia,Botta, Lorenzo,Fallacara, Anna Lucia,Falchi, Federico,Radi, Marco,Zamperini, Claudio,Dreassi, Elena,Dello Iacono, Lucia,Orioli, Donata,Biamonti, Giuseppe,Garbelli, Mirko,Lossani, Andrea,Gasparrini, Francesca,Tuccinardi, Tiziano,Laurenzana, Ilaria,Angelucci, Adriano,Maga, Giovanni,Schenone, Silvia,Brullo, Chiara,Musumeci, Francesca,Desogus, Andrea,Crespan, Emmanuele,Botta, Maurizio
p. 4590 - 4609
(2015/06/30)

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).
Vignaroli, Giulia,Mencarelli, Martina,Sementa, Deborah,Crespan, Emmanuele,Kissova, Miroslava,Maga, Giovanni,Schenone, Silvia,Radi, Marco,Botta, Maurizio
supporting information
p. 168 - 175
(2014/05/06)

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.
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Page/Page column 16

(2014/09/03)

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.
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Page/Page column 59

(2012/08/07)

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.
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Page/Page column 35-36

(2010/10/19)

PYRIMIDINE SUBSTITUTED MACROCYCLIC HCV INHIBITORS
Compounds of the Formula (I) including a stereoisomer thereof, or an N-oxide, a pharmaceutically acceptable addition salt, or a pharmaceutically acceptable addition solvate thereof; useful as HCV inhibitors; processes for preparing these compounds as well as pharmaceutical compositions comprising these compounds as active ingredient.
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Page/Page column 96

(2008/12/08)

Synthesis, molecular modeling and biological activity of methyl and thiomethyl substituted pyrimidines as corticotropin releasing hormone type 1 antagonists
Four small, targeted libraries of differentially substituted amino pyrimidines were synthesized in moderate to good yields. Excellent regiochemistry was observed for substitution at C2/C4 with selectivity >50 : 1 noted. All analogues were screened for their ability to interact with CRH 1 and CRH2 receptors. In all instances only poor agonistic and/or antagonistic behaviour was noted at CRH2. However, several compounds were potent and selective CRH1 antagonists, most notably 13a K1 = 39 nM. Additionally we have utilized these data and that recently reported by others to refine our original CRH1 pharmacophore (J. Med. Chem., 1999, 42, 2351-2357).
McCluskey, Adam,Keller, Paul A.,Morgan, Jody,Garner, James
p. 3353 - 3361
(2007/10/03)

7-(4,6-dimethoxypyrimidinyl)oxy- and -thiophthalides as novel herbicides: Part 1. CGA 279 233: A new grass-killer for rice
A series of novel types of 7-(4,6-dimethoxypyrimidin-2-yl)oxy - and -thio-3-methyl-1 (3H)-isobenzofuranones were discovered at Dr R Maag AG. From the thio-isobenzofuranyl series, CGA 279 233 - BSI-proposed common name pyriftalid - was chosen for further development as a grass herbicide for use in rice. General synthetic approaches to these new phthalic acid-derived compounds are given, with emphasis on the synthesis of pyriftalid and its physico-chemical behaviour.
Luethy, Christoph,Zondler, Helmut,Rapold, Thomas,Seifert, Gottfried,Urwyler, Bernhard,Heinis, Thomas,Steinruecken, Hans Christian,Allen, James
p. 205 - 224
(2007/10/03)

Herbicidal composition containing 2-benzyloxypyrimidine derivatives, processes for producing the derivatives and 2-benzyloxypyrimidine derivatives
A herbicidal composition comprising a herbicidally effective amount of a 2-benzyloxypyrimidine derivative represented by the formula (I): STR1 wherein R1 and R2 are each independently H, a halogen, hydroxyl, C1 -C4 alkyl, C1 -C4 haloalkyl, C3 -C5 alkenyl, C3 -C5 alkynyl, C1 -C4 alkoxy, C1 -C4 haloalkoxy, C3 -C5 alkenyloxy, C3 -C5 alkynyloxy, C1 -C4 alkylthio, or phenyl; n is an integer of 0 to 5; and each X which may be identical or different if n is greater than 1, is a halogen, C1 -C4 alkyl, C1 -C4 haloalkyl, C1 -C4 alkoxy, C1 -C4 alkylthio, C7 -C9 aralkyloxy, phenyl, hydroxymethyl, hydroxycarbonyl, C1 -C4 alkoxycarbonyl, or nitro, and an adjuvant.
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(2008/06/13)

Herbicidal substituted benzoylsulfonamides
Compound of the formula STR1 in which A is O, S, or NR3 ; G is CH or N; R and R1 are independently alkyl, alkoxy, haloalkoxy or alkylamino; R2 is phenyl, substituted phenyl, alkyl, cycloalkyl, haloalkyl or --CH2 [(R4)C(R5)n --Z; R3 and R7 are, independently, hydrogen, alkyl, --C(O)NH2 or --C(O)alkyl; R4 and R5 are independently hydrogen, alkyl, or halogen; R6 is halogen, alkyl, alkoxy, haloalkoxy, NO2, amino, alkyl substituted amino, or acyl substituted amino; n is 0 to 5; Z is cyano, amino, alkylamino, dialkylamino, --NHCO2 alkyl, alkoxy, alkylthio, alkylsulfonyl, alkenyl, alkynyl, phenyl or substituted phenyl; and Q is hydrogen, halogen, alkyl, alkoxy, haloalkoxy, nitro, amino, haloalkyl, alkythio, alkylsulfonyl, phenyl, substituted phenyl or phenoxy; or a 5 or 6 membered aromatic heterocycle having the formula STR2 in which "m" is 0 or 1; A' is O, S, or NR7 ; and X, X', Y, Y', W, W', V, V', U and Z' are independently N, O, S, --CH-- or --CR6. Intermediates for preparation of the benzoylsulfonamides are also disclosed.
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(2008/06/13)

Novel pyrimidine and 1,3,5-triazine hypolipidemic agents
New compounds were synthesized by changing the substituents of a trisubstituted pyrimidine, i.e., [[4-chloro-6-[(2,3-dimethylphenyl)amino]-2-pyrimidinyl]thio]acetic acid, a potent hypolipidemic agent, impaired, however, by a marked hepatomegaly-inducing effect. The structural variations led to the subsidence (14b, i.e., 4-chloro-2-(dimethylamino)-6-[(2,3-dimethylphenyl)amino]pyrimidine) or to the reduction (18b, [[4-chloro-6-[(2,3-dimethylphenyl)amino]-2-pyrimidinyl]amino]acetic acid) of said untoward effect but still maintained the hypolipidemic effect that, although markedly decreased, still proves significant for serum cholesterol and triglycerides (18b) or for serum triglycerides only (14b).
d'Atri,Gomarasca,Resnati,Tronconi,Scolastico,Sirtori
p. 1621 - 1629
(2007/10/02)