cas 113583-35-0, 2-Methylsulfonyl-4,6-dimethoxypyrimidine

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Design, Synthesis, and Herbicidal Activity of Pyrimidine-Biphenyl Hybrids as Novel Acetohydroxyacid Synthase Inhibitors
The issue of weed resistance to acetohydroxyacid synthase (EC 2.2.1.6, AHAS) inhibitors has become one of the largest obstacles for the application of this class of herbicides. In a continuing effort to discover novel AHAS inhibitors to overcome weed resistance, a series of pyrimidine-biphenyl hybrids (4aa-bb and 5aa-ah) were designed and synthesized via a scaffold hopping strategy. Among these derivatives, compounds 4aa (Ki = 0.09 μM) and 4bb (Ki = 0.02 μM) displayed higher inhibitory activities against Arabidopsis thaliana AHAS than those of the controls bispyribac (Ki = 0.54 μM) and flumetsulam (Ki = 0.38 μM). Remarkably, compounds 4aa, 4bb, 5ah, and 5ag exhibited excellent postemergence herbicidal activity and a broad spectrum of weed control at application rates of 37.5-150 g of active ingredient (ai)/ha. Furthermore, 4aa and 4bb showed higher herbicidal activity against AHAS inhibitor-resistant Descurainia sophia, Ammannia arenaria, and the corresponding sensitive weeds than that of bispyribac at 0.94-0.235 g ai/ha. Therefore, the pyrimidine-biphenyl motif and lead compounds 4aa and 4bb have great potential for the discovery of novel AHAS inhibitors to combat AHAS-inhibiting herbicide-resistant weeds.
Li, Ke-Jian,Qu, Ren-Yu,Liu, Yu-Chao,Yang, Jing-Fang,Devendar, Ponnam,Chen, Qiong,Niu, Cong-Wei,Xi, Zhen,Yang, Guang-Fu
p. 3773 - 3782
(2018)
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A novel pyrimidine-based stable-isotope labeling reagent and its application to quantitative analysis using matrix-assisted laser desorption/ionization mass spectrometry
As an extension of our previous work, a novel pyrimidine-based stable-isotope labeling reagent, [d0]-/[d6]-4,6-dimethoxy- 2-(methylsulfonyl)pyrimidine (DMMSP), was developed for comparative quantification of proteins by matrix-assisted laser desorption/ionization time-of-flight mass spectrometry (MALDI-TOF MS). Our one-step labeling strategy combines several desirable properties such as cysteine-specific labeling, signal amplification and direct analysis with minimum sample handling. All these features not only allow easy interpretation for protein identification and quantification but also ensure rapid and sensitive progression to MS analysis. Using cysteine, Cys-containing peptide, and lysozyme digest as model samples, the labeling methodology was established and the following pilot application for quantitative analysis was accomplished with high confidence, accuracy, efficiency, and reproducibility. The application of DMMSP-labeling strategy is expected to provide a powerful new tool for comparative proteome research, especially for the analysis of low-abundance proteins. Copyright
Zhang, Jing,Zhang, Li,Zhou, Ying,Guo, Yin-Long
p. 1514 - 1521
(2007)
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A facile synthesis of 4,6-dimethoxy-2-methylsulfonylpyrimidine
A facile and efficient synthesis of 4,6-dimethoxy-2-methylthiopyrimidine can be achieved by nucleophilic substitution of 2-chloro-4,6- dimethoxypyrimidine with sodium methyl mercaptide for a 95.6 % yield. 4,6-Dimethoxy-2-methylsulfonylpyrimidine can be produced via oxidation using hydrogen peroxide in the presence of sodium tungstate dihydrate in a 95 % yield.
Xu, Defeng,Zhu, Zhiling,Xu, Hui,Wang, Ziqiao
p. 313 - 314
(2014)
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A facile synthesis of [14C]pyrithiobac-sodium
Condensation of thiourea 1 with diethyl malonate 2 in the presence of sodium methoxide furnished 4,6-dihydroxy-2-mercaptopyrimidine 3. Compound 3 on methylation with diazomethane followed by oxidation with H5IO 6/CrO3 in ethyl acetate gave 4,6-dimethoxy-2- methylsulphonylpyrimidine 5. Compound 5 on condensation with 2-mercapto-6-chlorobenzoic acid in the presence of a phase transfer catalyst, tetrabutylammonium bromide and sodium carbonate gave the title compound - pyrithiobac-sodium 6 with an overall yield of > 35% starting from thiourea. Following the above standardized procedure, using [14C]-thiourea in lieu of thiourea, 14C labelled product 6, was synthesized with an overall radiochemical yield > 30% (with respect to [14C]-thiourea) for further evaluations of environmental fate of 6, in soils and plants. Copyright
Ravi,Mathew,Padmanabhan,Unny,Sivaprasad
p. 339 - 343
(2006)
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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; 0018-0019; 0020; 0022-0025

(2021/03/30)

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 17

(2014/09/03)

Synthesis and anti-inflammatory activity of 2-(2-aroylaroxy)-4,6-dimethoxy pyrimidines
Abstract-Reaction of 6a-f individually with 2-methylsulfonyl-4,6-dimethoxypyrimidine yielded 7a-f in excellent yield. The newly synthesized heterocycles were characterized by IR, 1H NMR, and mass spectral data. Compounds 7a-f was screened for their anti-inflammatory activity and were compared with standard drugs. Of the compounds studied, the compound 7e showed more potent activity than the standard drugs at all doses tested.
Venu,Khanum,Firdouse, Aiysha,Manuprasad,Shashikanth, Sheena,Mohamed, Riyaz,Vishwanth, Bannikuppe Sannanaik
scheme or table
p. 4409 - 4412
(2009/04/06)

Novel benzo[1,4]diazepin-2-one derivatives as endothelin receptor antagonists
Since its discovery in 1988 by Yanagisawa et al., endothelin (ET), a potent vasoconstrictor, has been widely implicated in the pathophysiology of cardiovascular, cerebrovascular, and renal diseases. Many research groups have embarked on the discovery and development of ET receptor antagonists for the treatment of such diseases. While several compounds, e.g., ambrisentan 2, are in late clinical trials for various indications, one compound (bosentan, Tracleer) is being marketed to treat pulmonary arterial hypertension. Inspired by the structure of ambrisentan 2, we designed a novel class of ET receptor antagonists based on a 1,3,4,5-tetrahydro-1H-benzo[e][1,4]diazepin-2-one scaffold. Here, we report on the preparation as well as the in vitro and in vivo structure-activity relationships of these derivatives. Potent dual ET A/ETB receptor antagonists with affinities in the low nanomolar range have been identified. In addition, several compounds efficiently reduced arterial blood pressure after oral administration to Dahl salt sensitive rats. In this animal model, the efficacy of the benzo[e] [1,4]diazepin-2-one derivative rac-39au was superior to that of racemic ambrisentan, rac-2.
Bolli, Martin H.,Marfurt, Judith,Grisostomi, Corinna,Boss, Christoph,Binkert, Christoph,Hess, Patrick,Treiber, Alexander,Thorin, Eric,Morrison, Keith,Buchmann, Stephan,Bur, Daniel,Ramuz, Henri,Clozel, Martine,Fischli, Walter,Weller, Thomas
p. 2776 - 2795
(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)

Rate acceleration of nucleophilic substitution of 2-chloro-4,6- dimethoxypyrimidine by sulfinate catalysis
The use of sulfinates greatly enhances the rate of substitution in the reaction of 2-chloro-4,6-dimethoxypyrimidine with alkoxy or aryloxy nucleophiles. Pyrimidinyloxy derivatives as intermediates for potent herbicides have been prepared in good yields fr
Bessard, Yves,Crettaz, Roger
p. 4739 - 4745
(2007/10/03)

Process for the preparation of substituted pyrimidines
A novel process for the preparation of substituted pyrimidine derivatives of the general formula: STR1 in which a halopyrimidine is reacted in the presence of a sulfinate with a compound selected from the series: STR2 The compounds of the general formula I are precursors of, for example, compounds with herbicidal activity.
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(2008/06/13)

Dimethoxypyrimidines as Novel Herbicides. Part 2. Synthesis and Herbicidal Activity of O-Pyrimidinylsalicylates and Analogues
A new series of the O-pyrimidinylsalicylates was synthesized and their herbicidal activity was examined. Some of these compounds showed very strong herbicidal activity under pre- and post-emergent treatment conditions against various kinds of grass and broadleaf weeds. Among these compounds, O-(4,6-dimethoxypyrimidin-2-yl)salicylic acid and its methyl ester were found to exhibit the highest activity. The herbicidal symptoms observed after the treatments included early cessation of plant growth followed by chlorosis, necrosis and plant death. The symptoms were similar to those caused by sulfonylureas and imidazolinones, which inhibit branched-chain acid biosynthesis.
Nezu, Yukio,Miyazaki, Masahiro,Sugiyama, Kazuhiko,Wada, Nobuhide,Kajiwara, Ikuo,Miyazawa, Takeshige
p. 115 - 124
(2007/10/03)

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)

Synthesis and anxiolytic activity of N-substituted cyclic imides (1R*,2S*3R*,4S*)-N-[4-[4-(2-pyrimidinyl)-1-piperazinyl]butyl]-2,3-b icyclo[2.2.1]heptanedicarboxime (Tandospirone) and related compounds
A series of cyclic imides bearing a ω-(4-aryl and 4-heteroaryl-1-piperazinyl)alkyl moieties was synthesized and tested in vivo for anxiolytic activity. The in vitro binding affinities of these compounds were also examined for 5-HT(1A) receptor sites. Structure-activity relationships within these series are discussed. One of these compounds, (1R*,2S*,3R*,4S*)-N-[4-[4-(2-pyrimidinyl)-1-piperazinyl]butyl]-2,3- bicyclo[2.2.1]heptanedicarboximide (1: tandospirone), was found to be equipotent with buspirone in its anxiolytic activity and more anxio-selective than buspirone and diazepam. Tandospirone (1) is currently undergoing clinical evaluation as a selective anxiolytic agent.
Ishizumi,Kojima,Antoku
p. 2288 - 2300
(2007/10/02)