Month: March 2022

Adding a certain compound to certain chemical reactions, such as: 87026-45-7, 4-Chloro-5-methoxy-2-(methylthio)pyrimidine, 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, Safety of 4-Chloro-5-methoxy-2-(methylthio)pyrimidine, blongs to pyrimidines compound. Safety of 4-Chloro-5-methoxy-2-(methylthio)pyrimidine

A round bottom flask containing ethyl formate (6 mL, 0.062 mol) and ethyl ether (30 mL) was placed in an ice water bath, Na (1.4 g, 0.062 mol) was added under stirring, and then methyl 2-methoxyacetate (6.5 g, 0.062 mol) was added dropwise. The mixture was stirred at room temperaturefor 4 h. The reaction was quenched by addition of ice water (25 mL), and the aqueous phase was separated. To the water layer, S-methyl isothiourea (5.6 g, 0.062 mol) and KOH (2.2 g, 0.062 mol) were added within 40 min, and then heated to 65 C for 1 h. After cooling, the reaction mixture was neutralized with 37% HCl. The crude product was collected by vacuum filtration, and then recrystallized with 95% ethanol to afford 2 as a white needle crystal (4.3 g, 40.1% yield). m.p. 193-195 C.The intermediate 2 (1.7 g, 0.01 mol) was added slowly into POCl3 (4.6 g, 0.03 mol) in ice-water bath, and then the mixture was heated to 80 C for 1 h until the reaction was completed. The reaction mixture was cooled to room temperature and neutralized with 25% ammonia water. The precipitated solid was filtered and recrystallized with petroleum ether, decolorized by activated carbon. The intermediate 3 was obtained as a light yellow solid (1.8 g, 95.2% yield). m.p. 74-75 C. The intermediate 3 was dissolved in methanol (10 mL), 50% hydrated hydrazine solution (1.6 g, 0.015 mol) was added dropwise in an ice-water bath. Then the mixture was heated to 50 C and monitored by TLC until the reaction was finished. After cooling, the solvent was removed under reduced pressure, and the solid was recrystallized from ethyl acetate and petroleum ether to afford 5-methoxy-2-(methylthio) pyrimidin-4-yl hydrazine (4, 1.1 g, 96.2%yield). m.p. 112-114 C.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,87026-45-7, 4-Chloro-5-methoxy-2-(methylthio)pyrimidine, and friends who are interested can also refer to it.

Reference:
Article; Song, Gaopeng; Li, Jianzuo; Tian, Hao; Li, Yasheng; Hu, Dekun; Li, Ying; Cui, Zining; Letters in drug design and discovery; vol. 13; 4; (2016); p. 329 – 334;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

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.147539-23-9, name is 1-Boc-4-(6-Chloro-5-nitro-4-pyrimidinyl)piperazine, molecular formula is C13H18ClN5O4, molecular weight is 343.77, as common compound, the synthetic route is as follows.category: pyrimidines

PREPARATION 10 1-[1,1-Dimethylethoxycarbonyl]-4-[5-amino-6-pyrimidinyl]piperazine A mixture of 1-[1,1-dimethylethoxycarbonyl]-4-[4-chloro-5-nitro-6-pyrimidyl]piperazine and triethylamine (0.3 ml) and palladium on carbon (5%, 0.13 g) in ethanol (100 ml) is charged with hydrogen gas (30 psi). After the theoretical amount of hydrogen gas is consumed, the catalyst is removed under reduced pressure. The filtrate is concentrated under reduced pressure to a foam which is diluted with an aqueous saturated solution of potassium carbonate and dichloromethane. The phases are separated and the organic phase is dried over sodium sulfate and concentrated to give to give the title compound, NMR (CDCl3) 1.49, 3.49, 3.29, 3.56, 7.98, and 8.39 delta.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,147539-23-9, 1-Boc-4-(6-Chloro-5-nitro-4-pyrimidinyl)piperazine, and friends who are interested can also refer to it.

Reference:
Patent; The Upjohn Company; US5599930; (1997); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

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. 53557-69-0, name is 6-Iodopyrimidin-4-amine. A new synthetic method of this compound is introduced below., COA of Formula: C4H4IN3

Step 2: 5-(6-Aminopyrimidin -yl)-2-(5-chloro-2-ethylphenyl)-1-(phenylsulfonyl)-1 H^yrrole-3-carbon (VI) 2-(5-Chloro-2-ethylphenyl)-1-(phenylsulfonyl)-5-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)-1 – -pyrrole-3-carbonitrile (2.77 mmol), 6-iodopyrimidin-4-amine (918 mg, 4.16 mmol), PdCI2(dppf) (226 mg, 0.277 mmol) and Cs2C03(2.71 g, 8.31 mmol) were degassed and back filled with argon and then dissolved in dioxane (20 mL) and water (4 mL) under nitrogen. The reaction mixture was stirred at room temperature over night, then diluted with EtOAc, washed with aqueous brine, dried over Na2S04, filtered and concentrated under reduced pressure. The residue was purified by Biotage SP1 Flash Chromatography (DCM/MeOH/NH37 N in MeOH 95/5/0.5) to afford the title compound (540 mg, 39%, 2 steps).1H NMR (600 MHz, DMSO-d6) delta 8.45 (d, J = 0.92 Hz, 1 H), 7.82 (t, J = 7.42 Hz, 1 H), 7.71 – 7.78 (m, 1 H), 7.59 – 7.63 (m, 1 H), 7.56 (dd, J = 2.29, 8.33 Hz, 1 H), 7.39 (d, J = 8.43 Hz, 1 H), 7.11 (br. s., 1 H), 7.09 (s, 1 H), 6.83 (d, J = 2.20 Hz, 1 H), 6.64 (d, J = 1.10 Hz, 1 H), 2.03 – 2.24 (m, 2H), 1.01 (t, J = 7.60 Hz, 3H).HRMS (ESI) m/z calcd for C23H18N502SCI + H+464.0943, found 464.0938.

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, 53557-69-0, 6-Iodopyrimidin-4-amine.

Reference:
Patent; NERVIANO MEDICAL SCIENCES S.R.L.; BRASCA, Maria Gabriella; BINDI, Simona; CALDARELLI, Marina; NESI, Marcella; ORRENIUS, Sten Christian; PANZERI, Achille; WO2014/19908; (2014); A2;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 76044-36-5, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 76044-36-5, name is 5-Chloro-[1,2,4]triazolo[1,5-c]pyrimidine, molecular formula is C5H3ClN4, The compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

To a solution of 5-choro-[I,2,4]triazoo[l,5-c]pyrimidine (120 mg, 776 mhio) in DMA (3.88 mL) was added (35,4;S)-3-methyl~2-oxa~8~azaspiro[4.5]decan-4-amine his hydrochloride (277 mg, 1.16 mmol) and DIPEA (675 m]_, 3.88 mmol). The reaction mixture was stirred in a capped vial at 90 C for 1 h. The resulting mixture was concentrated under reduced pressure and the crude residue was carried onto the next step without any further purification. LCMS (ESI): m/z: [M + H] calculated for C ui fuNA). 289.2; found 289.3.

While traditionally a conservative industry, chemical producers will need to modernize their PR strategies to stay relevant.we look forward to future research findings about 76044-36-5, 5-Chloro-[1,2,4]triazolo[1,5-c]pyrimidine.

Reference:
Patent; REVOLUTION MEDICINES, INC.; KOLTUN, Elena S.; AAY, Naing N.; BUCKL, Andreas; MELLEM, Kevin T.; BLANK, Brian R.; PITZEN, Jennifer; WANG, Gang; JOGALEKAR, Ashutosh S.; WON, Walter S.; TZITZILONIS, Christos; LI, Jie Jack; GILL, Adrian Liam; CREGG, James Joseph; (207 pag.)WO2019/118909; (2019); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 499195-60-7, 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.499195-60-7, name is Ethyl 4-(2-chloropyrimidin-4-yl)benzoate, molecular formula is C13H11ClN2O2, molecular weight is 262.69, as common compound, the synthetic route is as follows.

Step 1 : Preperation of ethyl 4-(2-((4-(4-(2-oxopyrrolidin-l-yl)piperidin-l-yl) phenyl) amino) pyrimidin-4-yl)benzoate. To a solution of ethyl 4-(2-chloropyrimidin-4-yl)benzoate (7.09 g, 27.0 mmol), in isopropyl alcohol [100 mL] was added l-(l-(4-aminophenyl)piperidin-4- yl)pyrrolidin-2-one (7.0 g, 27.0 mmol). To this, trifluoro acetic acid (4.62 g, 40.0 mmol) was added and mixture was heated at 120 C in sealed tube for 16 h. After completion of reaction, mixture was quenched in water, basified with ammonia solution and extracted with ethyl acetate. Organic layer was washed with water, dried over sodium sulfate and removed under reduced pressure to give crude off white solid compound. Purification of crude product was done by the way of column chromatography (Si02, hexane to 30 % EtOAc in hexane) to get solid compound (10.7 g, 82%). The title compound was characterized by spectral analysis. ESI-MS: 486.2 (M+H)+.

Statistics shows that 499195-60-7 is playing an increasingly important role. we look forward to future research findings about Ethyl 4-(2-chloropyrimidin-4-yl)benzoate.

Reference:
Patent; CADILA HEALTHCARE LIMITED; DESAI, Ranjit, C.; DESAI, Jigar; PATEL, Pankaj; WO2015/19365; (2015); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 1192711-71-9, name is 2,4-Dichloro-6-methyl-7H-pyrrolo[2,3-d]pyrimidine, the common compound, a new synthetic route is introduced below. HPLC of Formula: C7H5Cl2N3

General procedure: A mixture of 2,4-dichloro-7H-pyrrolo[2,3-d]pyrimidine 18a (51.3 g) and 1.36 L of 1 N NaOH was stirred at 80 C overnight. The solution was subsequently chilled and adjusted to pH 6 with AcOH. The resulting precipitate was collected, washed with water and dried to afford 19a as solid (37.3 g, yield: 80.7%).

The synthetic route of 1192711-71-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Xie, Hui; Zeng, Lili; Zeng, Shaogao; Lu, Xin; Zhang, Guicheng; Zhao, Xin; Cheng, Na; Tu, Zhengchao; Li, Zhiyuan; Xu, Hongjiang; Yang, Ling; Zhang, Xiquan; Huang, Min; Zhao, Junling; Hu, Wenhui; European Journal of Medicinal Chemistry; vol. 52; (2012); p. 205 – 212;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 554-01-8, 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 554-01-8, name is 5-Methylcytosine. This compound has unique chemical properties. The synthetic route is as follows.

General procedure: The basic system used in the study consisted of 0.1mM XBQ dissolved in acetonitrile (final acetonitrile concentration in the reaction mixture, 2%), 1.0mM H2O2, and 2.0mM 5mdC in 10mM phosphate buffer (pH 7.4) at 37C for 1h unless otherwise stated. The phosphate buffer used for all experiments was pretreated with Chelex-100 ion-exchange resin (Bio-Rad Laboratories, Hercules, CA, USA; 5g/L) overnight to remove trace transition metals probably present in phosphate buffer as contaminants. The reaction solutions were directly injected into an HPLC/triple-quadrupole mass spectrometry (HPLC-MS/MS) system for analysis.

According to the analysis of related databases, 554-01-8, the application of this compound in the production field has become more and more popular.

Reference:
Article; Shao, Jie; Huang, Chun-Hua; Kalyanaraman, Balaraman; Zhu, Ben-Zhan; Free Radical Biology and Medicine; vol. 60; (2013); p. 177 – 182;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

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.5270-94-0, name is 4,6-Dimethoxypyrimidine, molecular formula is C6H8N2O2, molecular weight is 140.14, as common compound, the synthetic route is as follows.HPLC of Formula: C6H8N2O2

B. Preparation of 5-bromo-4,6-dimethoxypyrimidine To the solution of 4,6-dimethoxypyrimidine (5 g, 35.7 mmol) in HOAc (20 mL) at room temperature under argon was added Ac2O (4.6 g, 44.6 mmol). The resulting solution was heated at 100 C. for 10 min and then NBS (7.9 g, 44.6 mmol) was added. Heating was continued at 100 C. for 5 h. Analysis by HPLC/MS indicated that the reaction was complete. After the reaction mixture was cooled to room temperature, water (50 mL) was added. The resulting precipitate was collected by filtration and further washed with water (15 mL*3), then dried under vacuum. The title compound (7.5 g) was obtained as a white solid. 1H NMR (CDCl3): delta 4.05 (s, 6H), 8.32 (s, 1H). 13C NMR (CDCl3): delta 55.2, 89.0, 154.9, 166.8.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,5270-94-0, 4,6-Dimethoxypyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; Wu, Gang; Mikkilineni, Amarendra B.; Sher, Philip M.; Murugesan, Natesan; Gu, Zhengxiang; US2006/287341; (2006); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

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. 31462-58-5, name is 5-Iodopyrimidine. This compound has unique chemical properties. The synthetic route is as follows. Safety of 5-Iodopyrimidine

General procedure: To 3-{2-[(tert-butyldimethylsilyl)oxy]ethyl}-13-{4-[5-chloro-2-(lH-l,2,3-triazol- 1 -yl)phenyl]-6-oxo- 1 ,2,3,6-tetrahydropyridin- 1 -yl} -9-methyl-3,4,7, 15-tetraazatricyclo [12.3.1.02’6]octadeca-l(18),2(6),4,14,16-pentaen-8-one was added MeOH (0.7 ml) and cone. HC1 (0.05 ml, 0.60 mmol) and the reaction was stirred for 10 min. The crude product was purified by reverse phase preparative HPLC to yield 13-{4-[5-chloro-2-(lH- 1,2,3-triazol- l-yl)phenyl]-6-oxo- 1,2,3, 6-tetrahydropyridin-l-yl}-3-(2-hydroxyethyl)-9- methyl-3 ,4,7, 15 -tetraazatricyclo[ 12.3.1.02’6] octadeca- 1 ( 18),2(6),4, 14, 16-pentaen-8-one as a white solid (6 mg, 8.22 muiotaetaomicron, 22.2% yield). NMR (500MHz, CD3OD) delta 8.76 – 8.70 (m, 1H), 8.34 – 8.30 (m, 1H), 7.93 – 7.88 (m, 1H), 7.84 – 7.78 (m, 1H), 7.68 – 7.62 (m, 3H), 7.60 (s, 3H), 5.89 – 5.81 (m, 1H), 5.59 – 5.50 (m, 1H), 4.44 – 4.38 (m, 2H), 4.05 – 3.97 (m, 3H), 3.51 – 3.45 (m, 2H), 2.61 – 2.51 (m, 1H), 2.23 – 2.09 (m, 3H), 1.99 – 1.81 (m, 2H), 1.65 – 1.53 (m, 1H), 1.39 – 1.28 (m, 2H), 1.19 – 1.12 (m, 2H), 1.12 – 1.08 (m, 3H). MS(ESI) m/z: 587.5 (M+H)+. Analytical HPLC (Method A): RT = 5.33 min, purity = 96%; Factor XIa Ki = 5.5 nM, Plasma Kallikrein Ki = 140 nM.(9R, 135)- 13- {4- [3 -Chloro-2-fluoro-6-(trifluoromethyl)phenyl]-6-oxo- 1,2,3,6- tetrahydropyridin- 1 -yl} -9-methyl-4-(pyrimidin-5-yl)-3 ,4,7, 15 -tetraazatricyclo[ 12.3.1.026] octadeca- 1(1 8),2,5,14,1 6-pentaen-8-one trifluoroacetate (7.5 mg, 9.85 imol, 18% yield)was prepared according to the procedures described in Example 11 by substituting (2-bromoethoxy)Qert-butyl)dimethylsilane with 5-iodopyrimidine. ?H NMR (500MHz,DMSO-d6) oe 9.58 (s, 1H), 9.39 (s, 2H), 9.19 (s, 1H), 8.80 (s, 1H), 8.68 (d, J=4.9 Hz, 1H),7.85 (t, J=7.8 Hz, 1H), 7.76 (s, 1H), 7.70 (d, J=8.5 Hz, 1H), 7.60 (d, J=4.3 Hz, 1H), 7.266.97 (m, 1H), 5.92 (s, 1H), 5.71 (d, J=8.8 Hz, 1H), 3.97 (br. s., 1H), 3.67 (br. s., 1H), 3.443.36 (m, 1H), 2.73 (br. s., 1H), 2.19 (br. s., 1H), 2.06 (br. s., 1H), 1.76 (br. s., 1H), 1.56(br. s., 1H), 1.34 (br. s., 1H), 0.97 (d, J=6.7 Hz, 3H), 0.69 (br. s., 1H). MS(ESI) m/z:640.1 [M+H]. Analytical HPLC (Method B): RT = 1.84 mm, purity = 99.0%; Factor XIaKi = 5.4 nM, Plasma Kallikrein Ki = 13 nM.

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, 31462-58-5, 5-Iodopyrimidine.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; DILGER, Andrew, K.; CORTE, James, R.; DE LUCCA, Indawati; FANG, Tianan; YANG, Wu; WANG, Yufeng; PABBISETTY, Kumar Balashanmuga; EWING, William, R.; ZHU, Yeheng; WEXLER, Ruth, R.; PINTO, Donald, J.P.; ORWAT, Michael, J.; SMITH II, Leon, M.; WO2015/116882; (2015); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 31462-58-5, Adding some certain compound to certain chemical reactions, such as: 31462-58-5, name is 5-Iodopyrimidine,molecular formula is C4H3IN2, 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 31462-58-5.

General procedure: In a typical experiment, 0.75 mg (0.03 mol%) of 3 was added into a mixture of aryl halide (1.0 mmol), olefin (2 mmol), Et3N (3 mmol) in DMF (2 mL), and the reaction mixture was stirred at 130 C. The formation of coupling product was monitored byTLC/GC analyses. After disappeared of the aryl halide (checking by TLC/GC), the reaction mixture was cold at room temperature and diluted with water and ethyl acetate and the solid Pd(II) complex 3 was separated by filtration. The cross-coupling product was extracted from the aqueous layer with ethyl acetate (3 x 5 mL), dried over MgSO4 and concentrated under reduced pressure. The crude product was purified by silica gel column chromatography (ethyl acetate/hexane) to give the corresponding cross-coupling product.

According to the analysis of related databases, 31462-58-5, the application of this compound in the production field has become more and more popular.

Reference:
Article; Sarkar, Shaheen M.; Rahman, Md. Lutfor; Chong, Kwok Feng; Yusoff, Mashitah Mohd; Journal of Catalysis; vol. 350; (2017); p. 103 – 110;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia