Month: May 2021

Reference of 5910-89-4, These common heterocyclic compound, 5910-89-4, name is 2,3-Dimethylpyrazine, 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.

The S-2-[3-(3-methylpyrazin-2-yl)isoxazol-5-yl]pyrrolidine starting material was prepared as follows: A mixture of 2,3-dimethylpyrazine (2Og, 18.5mmol), selenium dioxide (41.06g,25 37mmol) and diatomeous earth (2Og) in EtOAc (500ml) was stirred and heated at 7O0C for 2 hours. The mixture was allowed to cool and the insoluble matter was removed by filtration through diatomeous earth. The filtrate was washed with saturated aqueous sodium hydrogen carbonate solution and then saturated aqueous sodium chloride solution, dried (MgSO4) and the solvent removed by evaporation. The residue was suspended in water (100ml) and30 hydroxylamine (45ml of a 50% aqueous solution) was added. The mixture was stirred at ambient temperature for 18 hours and the mixture then extracted with EtOAc. The extracts were combined, washed with saturated aqueous sodium chloride solution, dried (MgSO4) and the solvent removed by evaporation. The residue was triturated with isohexane to give 3- EPO methylpyrazine-2-carboxaldehyde oxime (9.65g, 38%); NMR Spectrum 2.67 (s, 3H), 8.23 (s, IH), 8.45-8.49 (m, 2H), 11.87 (s, IH).

The synthetic route of 5910-89-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2006/109026; (2006); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

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. 5521-61-9, name is 6-Methylpyrazine-2-carboxylic acid, A new synthetic method of this compound is introduced below., Application In Synthesis of 6-Methylpyrazine-2-carboxylic acid

Step 2: methyl 5-(6-methylpyrazine-2-carboxamido)bicyclo[3.2.11 octane-l-carboxylateTo a solution of methyl 5-aminobicyclo[3.2.1 ]octane- l -carboxylate (0.98 g, 5.36 mmol) and 6-methylpyrazine-2-carboxylic acid (0.89 g, 6.45 mmol) in DCM (30 mL) and TEA (2 mL) was added PyBOP (3.35 g, 6.44 mmol). After stirring at room temperature overnight, water (30 mL) was added and the mixture was extracted with DCM (3 x 50 mL). The combined organic layer was washed with Sat. NaHC0 (50 mL) and brine (50 mL), dried over a2S04 and concentrated under reduced pressure. The residue was purified by column chromatography (silica gel, petroleum ether/ethyl acetate: 1/1 ) to afford 1 .28 g (79percent) of methyl 5-(6-methylpyrazine-2-carboxamido)bicyclo[3.2.1]octane-l -carboxylate as an off- white solid. ESI-MS m/z: 304 (M+H)+.

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; H. LUNDBECK A/S; LI, Guiying; ZHOU, Hao; WEISS, Jesse; DOLLER, Dario; FORD, James; WO2012/88365; (2012); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application of 476622-89-6, 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. 476622-89-6, name is 5-Bromo-2-iodo-3-methoxypyrazine belongs to pyrazines compound, it is a common compound, a new synthetic route is introduced below.

Step 1 . Synthesis of 5-bromo-3-methoxy-2-(4-methyl-1 /-/-imidazol-1 – yl)pyrazine (C11 ). A solution of 5-bromo-2-iodo-3-methoxypyrazine (which may be prepared according to Garg, N . K. et al., J. Am. Chem. Soc. 2002, 124, 13179- 13184) (92 g, 0.29 mol), 4-methyl-1 H-imidazole (38.5 g, 0.47 mol), K3P04 (157 g, 0.74 mol) and trans- ,2-diaminocyclohexane (15 mL, 0.12 mol) in dioxane (300 mL) was heated at reflux under a stream of argon for 15 minutes. Copper(l) iodide (5.5 g, 29 mmol) was added, and the reaction mixture was heated at reflux for an additional 30 minutes. After cooling to room temperature, the reaction mixture was diluted with ethyl acetate (1 .0 L) and chromatographed on silica (Gradient: 0% to 16% methanol in ethyl acetate) to provide the title compound. Yield: 21.7 g, 0.081 mol, 28%. 1 H N MR (400 MHz, CDCI3) delta 2.28 (s, 3H), 4.15 (s, 3H), 7.53 (s, 1 H), 8.08 (s, 1 H), 8.38 (s, 1 H).

The synthetic route of 5-Bromo-2-iodo-3-methoxypyrazine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PFIZER INC.; AM ENDE, Christopher William; JOHNSON, Douglas Scott; O’DONNELL, Christopher John; PETTERSSON, Martin Youngjin; SUBRAMANYAM, Chakrapani; WO2011/48525; (2011); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 77168-85-5 as follows. Quality Control of Methyl 5-chloro-6-methylpyrazine-2-carboxylate

[0145j A solution of methyl 5-chloro-6-methylpyrazine-2-carboxylate (1 g, 5.37 mmol) and potassium trimethyl silanolate (1.3 g, 10.7 mmol) in tetrahydrofuran (15 mL) was stirred at 70 °C under microwave irradiation for 20 minutes. Then the reaction mixture was acidified with iN hydrochloric acid to pH 3 and extracted with ethyl acetate (100 mL x 2). The combined organic extract was washed with brine (200 mL), dried over sodium sulfate and concentrated under vacuum to afford the title compound 5-chloro-6-methylpyrazine-2- carboxylic acid (0.800 g, crude) as a light yellow solid which was used for next step without further purification. Calculated M+H: 173.03; Found M+H: 173.33.

According to the analysis of related databases, 77168-85-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MNEMOSYNE PHARMACEUTICALS, INC.; ANDERSON, David R.; VOLKMANN, Robert A.; WO2015/48503; (2015); A2;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 213019-67-1, name is 3-(Trifluoromethyl)pyrazin-2-amine, belongs to pyrazines compound, 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 213019-67-1, Product Details of 213019-67-1

A solution of bromine in dichloromethane (10ml) was added in portions to a stirred solution of 2-amino-3-trifluoromethylpyrazine (1.5g, 9.2mmol) and pyridine (0.90ml, 1 1 mmol) in chloroform. The resulting mixture was stirred at room temperature for 24 hours. Volatiles were removed under reduced pressure and the residue was purified by chromatography on silica gel using a gradient of ethyl acetate in isohexane as eluent to give 2-amino-3-trifluoromethyl-5-bromopyrazine (1 .7g, 77%) as an off-white solid. (0286) 1H NMR (400MHz, CDCI3) delta 8.30 (s, 1 H), 5.13 (br s, 2H).

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.

Reference:
Patent; SYNGENTA PARTICIPATIONS AG; WAILES, Jeffrey, Steven; CARTER, Neil, Brian; CLOUGH, John, Martin; WILLIAMS, John; (57 pag.)WO2019/57723; (2019); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 74290-68-9, These common heterocyclic compound, 74290-68-9, name is 6-Bromo-5-methylpyrazin-2-amine, 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.

(4-Methoxy-2-methylphenyl)boronic acid (104 mg, 0.63 mmol), was combined with 6-bromo-5-methylpyrazin-2-amine (98 mg, 0.52 mmol) andtetrakis(triphenylphosphine)palladium(0) (31.6 mg, 0.03 mmol) in 1,4-dioxane (2 mL) and the reaction mixture was degassed with nitrogen. To this solution was added a degassed solution of sodium carbonate (166 mg, 1.56 mmol) in water (0.6 mL). After being heated in a microwave reactor at 130 00 for 2 hours, the reaction mixture was concentrated in vacuo. Purification via silica gel chromatography (Gradient: 40% to100% ethyl acetate in heptane) provided the product as a white solid. Yield: 111 mg,0.48 mmol, 93%. LCMS m/z 230.1 [M+H]. 1H NMR (400 MHz, CD3OD) oe 7.85 (5, 1H),7.08 (d, J=8.4 Hz, 1H), 6.87 (d, J=2.5 Hz, 1H), 6.84 (dd, J=8.0, 2.3 Hz, 1H), 3.82 (5,3H), 2.13 (5, 3H), 2.09 (5, 3H).

The synthetic route of 74290-68-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PFIZER INC.; GRAY, David Lawrence Firman; DAVOREN, Jennifer Elizabeth; DOUNAY, Amy Beth; EFREMOV, Ivan Viktorovich; MENTE, Scot Richard; SUBRAMANYAM, Chakrapani; WO2015/166370; (2015); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 40262-73-5, 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. 40262-73-5, name is 6-(4-Morpholinyl)pyrazine-2-carboxylic acid, This compound has unique chemical properties. The synthetic route is as follows.

(b) To a suspension of 2.50 g of 6-(4-morpholinyl) pyrazine-2-carboxylic acid in 50 ml of tetrahydrofuran, 3.60 ml of triethylamine and 1.60 ml of pivaloyl chloride were added dropwise successively at 0 C. under stirring. After stirring for 1 hour at 0 C., 1.12 g of 5-amino-1H-tetrazole was added to the mixture, and the reaction mixture was stirred for 1 hour at room temperature, and then refluxed for 12 hours. The reaction mixture was evaporated, and water was added to the residue. The precipitate was collected by filtration, and recrystallized from a mixture of dimethylsulfoxide and methanol affording 1.74 g of the desired compound as yellow needles. The obtained crystal was consistent with that of (a).

The chemical industry reduces the impact on the environment during synthesis 6-(4-Morpholinyl)pyrazine-2-carboxylic acid. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Hokuriku Pharmaceutical Co., Ltd.; US4792547; (1988); A;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 5910-89-4 as follows. Safety of 2,3-Dimethylpyrazine

A solution of 10.0 g (93.0 mmol) 2,3-dimethylpyrazine and 70.0 g (390 mmol) N-bromo- succinimide in 800 ml CCI4 is irradiated with a 250 Watt lamp at reflux temperature during 20 hours. After cooling the solution is filtered and the organic phase is washed with a 5% sodium thiosulfate solution and water. After evaporation of the organic phase, the residue is crystallised in ethanol to give 29.1 g (74%) of the title compound, m.p.: 167-1700C.

According to the analysis of related databases, 5910-89-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SYNGENTA PARTICIPATIONS AG,; WO2007/20050; (2007); A2;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 21943-15-7, 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. 21943-15-7, name is 3,5-Dibromo-2-hydroxypyrazine belongs to pyrazines compound, it is a common compound, a new synthetic route is introduced below.

General procedure: The suspension of 18b (2.51 g, 10.0 mmol), NaCN (0.59 g,12.0 mmol), CuI (0.95 g, 5.0 mmol) and Pd(PPh3)4 (0.14 g,0.1 mmol) were stirred in DMF (20 mL) at 120 C for 10 h under nitrogen protection. After cooling to room temperature, 10% aqueous solution of Na2S2O3(10 mL) and water(50 mL) were added. The mixture was extracted with ethyl acetate (50 mL × 3), washed with water (3 × 50 mL), dried over anhydrous Na2SO4 and concentrated. The residue was purified by chromatography on silica gel eluting with PE/EA (10:1-2:1) to give an off-white solid (1.1 g, yield 55%).

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 3,5-Dibromo-2-hydroxypyrazine, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Guo, Qi; Xu, Mingshuo; Guo, Shuang; Zhu, Fuqiang; Xie, Yuanchao; Shen, Jingshan; Chemical Papers; vol. 73; 5; (2019); p. 1043 – 1051;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

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. 1057216-55-3, name is 2-Chloro-5-iodopyrazine belongs to pyrazines compound, it is a common compound, a new synthetic route is introduced below. Product Details of 1057216-55-3

Step-a: Synthesis of 2-((5-iodopyrazin-2-yl)oxy)ethan-1-ol Into a 40-mL vial was placed 2-chloro-5-iodopyrazine (5.0 g, 20.80 mmol, 1.00 equiv), ethane-1,2-diol (3.36 g, 54.13 mmol, 2.60 equiv), sodium hydroxide (1.65 g, 41.25 mmol, 1.98 equiv), and NMP (5 mL). The resulting solution was stirred at 100 C. in an oil bath until completion. The reaction was then quenched by the addition of 200 mL water/ice. The solid was collected by filtration to deliver the title compound in 5.1 g (92%) as a light yellow solid. LCMS: 267 [M+H]+.

The synthetic route of 1057216-55-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; EISAI R & D MANAGEMENT CO., LTD.; BOCK, Mark; HAO, Ming-Hong; KORPAL, Manav; NYAVANANDI, Vijay Kumar; PUYANG, Xiaoling; SAMAJDAR, Susanta; SMITH, Peter Gerard; WANG, John; ZHENG, Guo Zhu; ZHU, Ping; MITCHELL, Lorna Helen; LARSEN, Nicholas; RIOUX, Nathalie; PRAJAPATI, Sudeep; REYNOLDS, Dominic; O’SHEA, Morgan; SAMARAKOON, Thiwanka; (134 pag.)US2018/141913; (2018); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem