The origin of a common compound about 6-Chloro-1-methylpyrimidine-2,4(1H,3H)-dione

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Related Products of 31737-09-4, The major producers of chemicals have been the Europe, Japan and China. Due to the growing call for a cleaner, greener environment, people will have to find innovative ways to maintain their relevance. Here is a compound 31737-09-4, name is 6-Chloro-1-methylpyrimidine-2,4(1H,3H)-dione. This compound has unique chemical properties. The synthetic route is as follows.

Intermediate 1 (300 mg, 1 eq.) and tetrahydropyrrole (930 ul, 6 eq.) were dissolved in 5 ml of absolute ethanol and stirred at 70 C for 0.5 h. After the mixture was cooled, the ethanol was distilled off and water was added. The mixture was extracted twice with dichloromethane, rinsed once with saturated brine, dried over magnesium sulfate, filtered and the solvent was evaporated to give 310 mg of intermediate 4a. MS (ESI): 196 (M+H)

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Reference:
Patent; Shanghai Institute Of Materia Medica Chinese Academy of Sciences; SHEN, Jianhua; WANG, Yiping; CHEN, Xinde; XU, Wenwei; WANG, Kai; (84 pag.)EP3239135; (2017); A1;,
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New learning discoveries about 6-Chloro-1-methylpyrimidine-2,4(1H,3H)-dione

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Adding a certain compound to certain chemical reactions, such as: 31737-09-4, 6-Chloro-1-methylpyrimidine-2,4(1H,3H)-dione, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound, Product Details of 31737-09-4, blongs to pyrimidines compound. Product Details of 31737-09-4

To a stirred solution of 6-chloro-1-methyl-1,2,3,4-tetrahydropyrimidine-2,4-dione (3 g, 18.68 mmol, 1 equiv.) and tert-butyl piperazine-1-carboxylate (4.2 g, 22.42 mmol, 1.2 equiv.) in EtOH (60 mL) was added NaHCO3(3.1 g, 37.37 mmol, 2 equiv.) at room temperature. The mixture was stirred at 70 degrees Celsius for 5 h. The mixture was concentrated under reduced pressure. The residue was purified by silica gel column chromatography, eluted with CH2Cl2/ MeOH (15:1 to 10:1) to afford tert-butyl 4-(3-methyl-2,6-dioxo-1,2,3,6-tetrahydropyrimidin-4- yl)piperazine-1-carboxylate(5.38 g, 92.78%) as a white solid.

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Reference:
Patent; GOLDFINCH BIO, INC.; YU, Maolin; DANIELS, Matthew, H.; HARMANGE, Jean-christophe, P.; TIBBITTS, Thomas, T.; LEDEBOER, Mark, W.; WALSH, Liron; MUNDEL, Peter, H.; MALOJCIC, Goran; (860 pag.)WO2019/55966; (2019); A2;,
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Extended knowledge of 6-Chloro-1-methylpyrimidine-2,4(1H,3H)-dione

At the same time, in my other blogs, there are other synthetic methods of this type of compound,31737-09-4, 6-Chloro-1-methylpyrimidine-2,4(1H,3H)-dione, and friends who are interested can also refer to it.

With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.31737-09-4, name is 6-Chloro-1-methylpyrimidine-2,4(1H,3H)-dione, molecular formula is C5H5ClN2O2, molecular weight is 160.5584, as common compound, the synthetic route is as follows.Application In Synthesis of 6-Chloro-1-methylpyrimidine-2,4(1H,3H)-dione

6-Chloro-1-methyluracil (250 mg; 1.56 mmol) was dissolved in aniline (500 mg; 5.4 mmol) and stirred at 150 C for 90 min. The solid mixture obtained was washed with ether and methanol and dried. White crystals (304 mg; 90%) were obtained. Mp 308-310 C. 1H NMR (DMSO-d6, 25 C, 500.1 MHz), delta: 3.39 (s, 3H, N-CH3); 4.51 (s, 1H, CH), 7.20-7.27 (m, 3H, Ar-H); 7.36-7.45 (m, 2H, Ar-H); 8.55 (s, 1H, NH);13C NMR (DMSO-d6, 25 C, 125.8 MHz), delta: 25.93, 77.91, 123.06, 125.53, 129.79, 138.92, 151.72, 155.35, 162.95; HR-MS (ESI), calcd for C11H11N3O2 m/z [M+Na]+ = 240.07435, found = 240.07468.

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Reference:
Article; Hartman, Tomas; Herzig, Vladimir; Budesinsky, Milos; Jindrich, Jindrich; Cibulka, Radek; Kraus, Tomas; Tetrahedron Asymmetry; vol. 23; 22-23; (2012); p. 1571 – 1583;,
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Brief introduction of 31737-09-4

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Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 31737-09-4, name is 6-Chloro-1-methylpyrimidine-2,4(1H,3H)-dione. This compound has unique chemical properties. The synthetic route is as follows. COA of Formula: C5H5ClN2O2

Intermediate 1 (300 mg, 1 eq.), phenylboronic acid (296 mg, 1.3 eq.), tetrakis(triphenylphosphine)palladium (108 mg, 0.05 eq.) and 2N aqueous sodium carbonate solution (654ul, 3 eq.) were mixed in 5 ml of glycol dimethyl ether and reacted under microwave at 120 C for 50 min. The mixture was cooled and evaporated to remove solvent. Water was added and the mixture was extracted with dichloromethane twice, rinsed with saturated brine once, dried over sodium sulfate, filtered, and evaporated to remove solvent to give 310 mg of intermediate 23a. MS (ESI): 203(M+H)

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it, 31737-09-4, 6-Chloro-1-methylpyrimidine-2,4(1H,3H)-dione.

Reference:
Patent; Shanghai Institute Of Materia Medica Chinese Academy of Sciences; SHEN, Jianhua; WANG, Yiping; CHEN, Xinde; XU, Wenwei; WANG, Kai; (84 pag.)EP3239135; (2017); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Extracurricular laboratory: Synthetic route of 31737-09-4

According to the analysis of related databases, 31737-09-4, the application of this compound in the production field has become more and more popular.

Related Products of 31737-09-4, Adding some certain compound to certain chemical reactions, such as: 31737-09-4, name is 6-Chloro-1-methylpyrimidine-2,4(1H,3H)-dione,molecular formula is C5H5ClN2O2, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 31737-09-4.

Scheme 85 represents an alternative method of synthesizing compounds of formula [I-EII.] Briefly, compound IX, which is prepared as described in [KAZIMIERCZUK,] et al., Intermediates in the synthesis of purines and [PTERIDINES] : N- methylated 6-chlorouracils, Acta Biochim. Pol. (1970), 17 (4), 325-9; Pfleider, et al. , Liebigs Ann. Chem, 612,158, (1958); and Hirota, et al. , Pyrimidines. 65. Synthesis of 6-substituted thieno [2,3-d] pyrimidine-2,4 (1H, 3H)-diones, J. Heterocycl. Chem. (1990), 27 (3), 717-21; each of which are incorporated herein by reference, is reacted with 3,4-di-fluorobenzyl bromide (1.1 equiv. ) in DMF at room temperature for 18 hours in the presence of cesium carbonate 1.5 equiv. ) to give product X. Reaction of X (1.0 equiv. ) with thiogylcolic acid ethyl ester (1.0 equiv. ) in room temperature ethanol in the presence of triethyl amine (1.0 equiv. ) for 1.5 hour provided [[1- (3,] 4-Difluoro-benzyl) -3-methyl-2, 6-oxo-1, 2,3, 6-tetrahydro- [PYRIMIDIN-4-YLSULFANYL]-ACETIC] acid ethyl ester, compound XI. This material is treated with POC13 (1.2 equiv. ) and DMF (1.1 equiv. ) in methylene chloride at [0 XB0;C] to reflux under Vilsmeier-Haack conditions to provide [FORMYLATED] product XII. Heating this material in the presence of sodium carbonate (1.5 equiv. ) in ethanol at-reflux for 18 hours provides the cyclized product [3- (3,] 4-difluoro- [BENZYL)-1-METHYL-2,] 4-dioxo-1,2, 3,4-tetrahydro-thieno [2,3-d] pyrimidine-6- carboxylic acid ethyl ester XIII. Saponification of XIII with sodium hydroxide sodium hydroxide (1.2 equiv) in methanol/water (1: 1) mixture at room temperature for 18 hours gives XIV. EDAC HCl (1.3 equiv. ) coupling of XIV in DMF with [3- (OR 4-)- (Z-L)-BENZYLAMINE] (1.3 equiv. ), and HOBT (1.3 equiv. ) for 18 hours at room temperature provided [Z-L- {3- (3, 4-DIFLUORO-BENZYL)-1-METHYL-] 2, 4-oxo-1, 2,3, 4-tetrahydro-thieno [2,3-d] pyrimidine-6-carboxylic acid [BENZYLAMIDE}] XV.

According to the analysis of related databases, 31737-09-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; WARNER-LAMBERT COMPANY LLC; WO2004/14384; (2004); A2;,
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Analyzing the synthesis route of 6-Chloro-1-methylpyrimidine-2,4(1H,3H)-dione

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,31737-09-4, its application will become more common.

Electric Literature of 31737-09-4, Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps,and cheap raw materials. 31737-09-4, name is 6-Chloro-1-methylpyrimidine-2,4(1H,3H)-dione. A new synthetic method of this compound is introduced below.

Intermediate 49 was prepared from Intermediate 4 and Intermediate 46 by a method analogous to that of Step 1 of Example 1, Yield 81.8%. Step 1: Preparation of 1-(2-butyn-1-yl)-6-chloropyrimidine-2,4(1H,3H)-dione (Intermediate 1) 6-chlorouracil (14.5 g, 100 mmol) was dissolved in a mixed solution of 150 mL of N,N-dimethylformamide (DMF) / dimethylsulfoxide (DMSO) (VDMF / VDMSO = 6: 1), cooled to 0C, adding sodium hydride (4.2 g, 105 mmol). After stirring for 5 min, lithium bromide (13.0 g, 105 mmol) was added, stirring was continued for 15 min, then 1-bromo-2-butyne (14.0 g, 105 mmol) in N,N-dimethylformamide solution (50 mL) was added dropwise thereto, followed by stirring at room temperature for 10 to 12 hours. After completion of the reaction, the reaction solution was poured into ice water, and the precipitated solid was stirred, filtered and vacuum dried to obtain 17.0 g of a light yellow solid in a yield of 85.6%

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,31737-09-4, its application will become more common.

Reference:
Patent; Qilu Pharmaceutical Co.,Ltd.; Chen, Dong; Fan, Chuanwen; He, Xujun; Cheng, Zhe; Li, Chenglong; (36 pag.)CN103848811; (2016); B;,
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Pyrimidine – Wikipedia