Day: February 3, 2021

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. 941685-26-3, name is 4-Chloro-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidine, the common compound, a new synthetic route is introduced below. Formula: C12H18ClN3OSi

Step 1: 4-chloro-6-methyl-7-{[2-(trimethylsilyl)ethoxy]methyl-7H-pyrrolo[2,3d]pyrimidine To a stirred solution of Intermediate 2a (100 mg, 0.352 mmol) in THF (1 mL) was added LDA (2.0M; 0.19 mL, 0.39 mmol) dropwise at -78 C. The reaction mixture was stirred at this temperature for 40 minutes, then MeI (0.11 mL, 1.8 mmol) was added and the reaction was stirred at -78 C for an additional 40 minutes before being quenched with EtOAc and poured into a mixture of EtOAc and silica gel. The resulting mixture was concentrated in vacuo to afford a crude solid that was purified by column chromatography on silica gel, eluting with EtOAc/hexane (2-20%) to afford the desired product as a colorless oil. LRMS calc’d for C13H21ClN3OSi [M+H]+, 298; found 298. 1H NMR (500 MHz, CDCl3) delta 8.60 (s, 1H), 6.40 (s, 1H), 5.65 (s, 2H), 3.51 (t, 2H), 2.56 (s, 3H), 0.90 (t, 2H), 0.06 (s, 9H).

The synthetic route of 941685-26-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Merck Sharp & Dohme Corp.; GUERIN, David Joseph; BRUBAKER, Jason, D.; MARTINEZ, Michelle; JUNG, Joon, O.; ANTHONY, Neville, J.; SCOTT, Mark, E.; HOFFMAN, Dawn Marie Mampreian; WOO, Hyun Chong; DINSMORE, Christopher, J.; (75 pag.)EP2629777; (2018); B1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 932-52-5, 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. 932-52-5, name is 5-Aminopyrimidine-2,4(1H,3H)-dione. A new synthetic method of this compound is introduced below.

General procedure: To a mixture of 5-aminouracil (127 mg, 1 mmol) with an appropriate aldehyde (241 mg, 1.2 mmol) in methanol (15 mL) were added few drops of glacial acetic acid. The reaction mixture was stirred at room temperature until 5-aminouracil was completely consumed (TLC). The precipitate was filtered off, washed with methanol and air dried to give the corresponding product 1-10 as a yellow solid.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,932-52-5, its application will become more common.

Reference:
Article; Koz; Russian Journal of General Chemistry; vol. 89; 1; (2019); p. 122 – 127; Zh. Obshch. Khim.; vol. 89; 1; (2019); p. 122 – 127,6;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 24391-41-1, 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 24391-41-1, name is 4-Chloro-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile. This compound has unique chemical properties. The synthetic route is as follows.

A mixture of 14b (0.132 mmol), 4-chloro-7H-pyrrolo[2,3-d]pyrimidine-5- carbonitrile (24 mg, 0.132 mmol) and TEA (0.09 mL, 0.66 mmol) in n-BuOH (10 mL) was heated at reflux for 2 hours. The reaction mixture was concentrated purified by flash column chromatography eluting with MeOH/water to afford compound 107 as a slight yellow solid (17 mg, yield: 31%). MS (m/z): 420.7 (M+H)+. 1H-NMR (400 MHz, DMSO-d6) delta: 8.29 (s, 1H), 8.03 (s, 1H), 6.77 (t, J= 5.1 Hz, 1H), 6.16 (t, J= 4.0 Hz, 1H), 5.55-5.45 (m, 1H), 4.30-4.22 (m, 1H), 4.18-4.05 (m, 2H), 3.71-3.67 (m, 1H), 2.37-2.01 (m, 5H), 1.00 (d, J= 6.6 Hz, 3H), 0.93 (d, J= 6.5 Hz, 3H).

According to the analysis of related databases, 24391-41-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; HUTCHISON MEDIPHARMA LIMITED; SU, Wei-guo; DAI, Guangxiu; XIAO, Kun; JIA, Hong; ZHANG, Zhulin; VENABLE, Jennifer Diane; BEMBENEK, Scott Damian; CHAI, Wenying; WO2014/15830; (2014); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 49844-90-8, 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. 49844-90-8, name is 4-Chloro-2-(methylthio)pyrimidine, molecular formula is C5H5ClN2S, 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.

4-Chloro-2-(methylthio)pyrimidine (XII) (19.8 g, 123.4 mmol),Methyl 2-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate(III) (34.1 g, 123.4 mmol), tetrakistriphenylphosphine palladium (7.1 g, 6.17 mmol) and sodium carbonate (26.2 g, 246.8 mmol) in toluene (90 mL), methanol (30 mL) and water (30 mL) In the mixed solvent of the composition, under nitrogen protection, the reaction is carried out at 70 C for about 8 h, and the raw materials are to be detected by TLC (petroleum ether: ethyl acetate = 10:1).The reaction was completed, the mixture was cooled to room temperature, ethyl acetate (100 mL) was added, and the mixture was partitioned, and the solvent was evaporated to dryness.Obtained 29.8 g of a white solid, yield: 88.0%

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 49844-90-8, 4-Chloro-2-(methylthio)pyrimidine.

Reference:
Patent; China Pharmaceutical University; Xu Yungen; Ji Dezhong; Zhang Lingzhi; Zhu Qihua; Bai Ying; Wu Yaoyao; (41 pag.)CN109608444; (2019); 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. 582313-57-3, name is 4-Chloro-5-fluoro-7H-pyrrolo[2,3-d]pyrimidine. A new synthetic method of this compound is introduced below., Recommanded Product: 4-Chloro-5-fluoro-7H-pyrrolo[2,3-d]pyrimidine

4.1.11 7-(2-O-Acetyl-3,5-di-O-benzyl-4-C-methyl-beta-d-ribofuranosyl)-4-chloro-5-fluoro-7H-pyrrolo[2,3-d]pyrimidine (12) To a slurry of 4-chloro-5-fluoro-7H-pyrrolo[2,3-d]pyrimidine 11 (2.06 g, 12 mmol) in dry MeCN (20 ml) was added N,O-bis(trimethylsilyl)acetamide [BSA] (2.94 ml, 9.55 mmol) and the mixture was stirred at rt for 15 min (clear solution). Then a solution of 1,2-di-O-acetyl-3,5-di-O-benzyl-4-C-methyl-beta-d-ribofuranose 5 (5.14 g, 12 mmol) in MeCN (40 ml) was added, followed by TMSOTf (4.34 ml, 24 mmol). The solution was stirred at 80 ¡ãC for 3 h. After cooling, the mixture was diluted with EtOAc (200 ml), cautiously washed with saturated aq NaHCO3 (100 ml) and aqueous phase was re-extracted with EtOAc (2 * 25 ml). Combined organic phases were dried (MgSO4), concentrated in vacuo and loaded on silica by co-evaporation. Column chromatography (SiO2, hexane-AcOEt, 10:1) afforded nucleoside 12 as yellowish oil (3.76 g, 58percent). 1H NMR (500 MHz, CDCl3): 1.32 (s, 3H, CH3-4′); 2.05 (s, 3H, CH3CO); 3.40 (d, 1H, Jgem = 10.2 Hz, H-5’a); 3.56 (d, 1H, Jgem = 10.2 Hz, H-5’b); 4.42 (d, 1H, J3′,2′ = 5.7 Hz, H-3′); 4.48 (bd, 1H, Jgem = 11.5 Hz, CH2a-Bn-5′); 4.50 (d, 1H, Jgem = 11.5 Hz, CH2a-Bn-3′); 4.56 (d, 1H, Jgem = 11.5 Hz, CH2b-Bn-5′); 4.60 (d, 1H, Jgem = 11.6 Hz, CH2b-Bn-3′); 5.56 (bt, 1H, J2′,3′ = J2′,1′ = 5.3 Hz, H-2′); 6.62 (dd, 1H, J1′,2′ = 5.0 Hz, J1′,F = 1.8 Hz, H-1′); 7.29-7.41 (m, 11H, H-o,m,p-Bn-3′,5′, H-6); 8.59 (s, 1H, H-2). 13C NMR (125.7 MHz, CDCl3): 18.99 (CH3-4′); 20.69 (CH3CO); 73.64 (CH2-Bn-5′); 74.18 (CH2-Bn-3′); 74.43 (CH2-5′); 75.97 (CH-2′); 77.79 (CH-3′); 85.00 (CH-1′); 86.30 (C-4′); 107.58 (d, JC,F = 14.4 Hz, C-4a); 109.64 (d, JC,F = 27.0 Hz, CH-6); 127.86 and 127.97 (CH-o-Bn-3′,5′); 128.03 and 128.11 (CH-p-Bn-3′,5′); 128.45 and 128.62 (CH-m-Bn-3′,5′); 137.21 (C-i-Bn-5′); 137.57 (C-i-Bn-3′); 141.60(d, JC,F = 253.6 Hz, C-5); 147.04 (d, JC,F = 1.2 Hz, C-7a); 150.46 (d, JC,F = 3.7 Hz, C-4); 151.50 (CH-2); 169.93 (CO). 19F NMR (470.3 MHz, DMSO-d6): -167.38 (s, 1F, F-5). IR (ATR): nu 1678, 1622, 1593, 1457, 1231, 1070, 1028, 741, 700 cm-1. MS (ESI) m/z 540 (M+H), 562 (M+Na). HRMS (ESI) for C28H27O5N3ClFNa [M+Na] calcd: 562.15155; found: 562.15140.

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, 582313-57-3, 4-Chloro-5-fluoro-7H-pyrrolo[2,3-d]pyrimidine.

Reference:
Article; Nau?, Petr; Caletkova, Olga; Perlikova, Pavla; Po?tova Slav?tinska, Lenka; Tlou??ova, Eva; Hodek, Jan; Weber, Jan; D?ubak, Petr; Hajduch, Marian; Hocek, Michal; Bioorganic and Medicinal Chemistry; vol. 23; 23; (2015); p. 7422 – 7438;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 5305-59-9, 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. 5305-59-9, name is 6-Chloropyrimidin-4-amine, molecular formula is C4H4ClN3, 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.

The 200 mg (1equiv) 4-amino-6-chloro-pyrimidine, 152 mg (1.2equiv) 4-methyl imidazole, 604 mg (1.2equiv) adding cesium carbonate flask, 10mLN, N ‘-dimethyl formamide as a solvent, the temperature is increased to 120 C, reaction 12h. Adding proper amount of water, extraction with ethyl acetate, saturated salt water washing, drying by anhydrous sodium sulfate, filter, evaporate solvents under reduced pressure, the residue is purified by silica gel column chromatography separation, methanol/dichloromethane = 1/20 elution, to get the yellow solid 176 mg, yield 65%.

According to the analysis of related databases, 5305-59-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; East China University of Technology; Mao, Fei; Wang, Huan; Li, Xiaokang; Zhang, Haiyan; Lu, Zhengyu; Li, Jian; (43 pag.)CN105418592; (2016); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 3764-01-0, 2,4,6-Trichloropyrimidine, 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, Computed Properties of C4HCl3N2, blongs to pyrimidines compound. Computed Properties of C4HCl3N2

Take 5000ml three necked flask, equipped with mechanical stirrer, condenser. Feed: 18.2 g of 2,4,6-trichloropyrimidine (molecular weight 182,0.10 mol), phenylboronic acid 28.1 g (molecular weight 122,0.23 mol), tetrakis(triphenylphosphine)palladium 12.0g (0.0104mol), potassium carbonate 60 g (0.435 mol), tetrahydrofuran 600 ml, toluene 400 ml, water 400 ml. Mechanical agitation was initiated under conditions of reduced pressure ventilation Ar gas three times to maintain protection, monitoring the reaction by TLC (thin layer chromatography), refluxed for 8 hours, the reaction was complete. Allowed to cool, the reaction system was divided into two layers, the organic layer was separated and evaporated to dryness to give a solid product, which was recrystallized from toluene to give intermediate M3-1 was 19.9 g, molecular weight 266, 75% yield.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,3764-01-0, 2,4,6-Trichloropyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; Kunshan Visionox Display Technology?Co., Ltd; Tsinghua University; Beijing Visionox Technology Co. Ltdk; QIU, YONG; TANG, JINMING; FAN, HONGTAO; DUAN, LIAN; REN, XUEYAN; (97 pag.)CN103664906; (2016); B;,
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. 33034-67-2, name is 2-Chloro-4-(trifluoromethyl)pyrimidine. This compound has unique chemical properties. The synthetic route is as follows. Recommanded Product: 2-Chloro-4-(trifluoromethyl)pyrimidine

General procedure: alpha,beta-unsaturated tosylhydrazones 1 (0.11 mmol, 1.1 equiv), heteroaryl chlorides 2 (0.1 mmol, 1 equiv), Cs2CO3 (0.25 mmol, 2.5 equiv) and MeCN (1 mL) were added to a tube. The mixture was stirred at 60 C until the heteroaryl chlorides was completely disappeared for 4-8h. After cooling to room temperature, the mixture was quenched with NH4Cl (2 mL, saturated aqueous solution) and extracted with CH2Cl2 (3 ¡Á 2 mL). The combined organic phases were dried over Na2SO4 and solvents removed in vacuo. The residue was purified by flash column chromatography on silica gel with ethyl acetate/petroleum ether (1:10-1:4, V/V) as the eluent, affording the desired product 3 and 4.

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, 33034-67-2, 2-Chloro-4-(trifluoromethyl)pyrimidine.

Reference:
Article; Zeng, Lin; Guo, Xiao-Qiang; Yang, Zai-Jun; Gan, Ya; Chen, Lian-Mei; Kang, Tai-Ran; Tetrahedron Letters; vol. 60; 33; (2019);,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 6299-85-0, Methyl 2,6-dichloropyrimidine-4-carboxylate, 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, Recommanded Product: Methyl 2,6-dichloropyrimidine-4-carboxylate, blongs to pyrimidines compound. Recommanded Product: Methyl 2,6-dichloropyrimidine-4-carboxylate

Example 226 (Z)-methyl 2-(((1-(4-((2,4-dioxothiazolidin-5-ylidene)methyl)pyrimidin-2-yl)piperidin-4-yl)methyl)amino)pyrimidine-4-carboxylate was prepared as follows.Methyl 2-((piperidin-4-ylmethyl)amino)pyrimidine-4-carboxylate was prepared as follows: A 40 mL round-bottomed vial was charged with tert-butyl 4-(aminomethyl)piperidine-1-carboxylate (1.76 mmol, 1.1 equiv.), acetonitrile (4 mL), DiPEA (2.37 mmol, 1.5 equiv.), methyl 2,6-dichloropyrimidine-4-carboxylate (1.58 mmol, 1 equiv.), and then shaken at 85 C. for 72 h. The reaction mixture was concentrated under reduced pressure and purified on SiO2 using a Biotage and a 10-50% EtOAc/hexanes gradient to provide the desired protected amine (233 mg, 552 mg theoretical, 42%). Methyl 2-((piperidin-4-ylmethyl)amino)pyrimidine-4-carboxylate was prepared using the general TFA de-protection procedure and used directly in the general displacement procedure to provide the title compound (4 mg, 73.4 mg theoretical, 5%). LC-MS m/z 456.1 (M+1).

The synthetic route of 6299-85-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Jasco Pharmaceuticals, LLC; US2011/152235; (2011); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 14048-15-8 , The common heterocyclic compound, 14048-15-8, name is 2,4-Dimethoxypyrimidin-5-amine, molecular formula is C6H9N3O2, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route.

Reference Example 95 5-Isothiocyanato-2,4-dimethoxypyrimidine To a solution of 2,4-dimethoxypyrimidin-5-amine (prepared by the method described in U.S. Pat. No. 6,342,503B1) (4.68 g, 30.0 mmol) in tetrahydrofuran (60 mL) was added 1,1-thiocarbonyldiimidazole (6.41 g, 36.0 mmol) portionwise at 0 C. The mixture was warmed to room temperature and stirred for 20 hr. The mixture was concentrated in vacuo to give a residue which was passed through a pad of silica gel eluding with n-hexane/ethyl acetate. The filtrate was concentrated in vacuo to give the title compound (5.0 g, 84%) as a colorless solid. 1H NMR (CDCl3) delta 3.99 (s, 3H), 4.09 (s, 3H), 8.06 (s, 1H). MS Calcd.: 197; Found: 198 (M+H).

The synthetic route of 14048-15-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; US2009/186879; (2009); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia