Category: 914452-71-4

Synthetic Route of 914452-71-4, 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. 914452-71-4 name is 2-Bromo-6-methylpyrazine, This 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 2-bromo-6-methyl-pyrazine 53-3 (875.52 mg, 5.06mmol) and methyl 1- chloropiperidine-4-carboxylate 53-2 (1000 mg, 5.57mmoi) in toluene (25 mL) was added cesium carbonate (4.95 g, 15.18 mmol). The reaction was degassed with argon for 10 minutes. Xanthphos (146.40 mg, 253.03 umol) and Pd2(dba>3 (231.70 mg, 253.03 umol) were added and the mixture was heated at 90C for 16 hours. The reaction was then cooled to room temperature and diluted with ethyl acetate. Organic layer was washed with water and brine, dried over sodium sulfate, concentrated under reduced pressure, and purified by combiflash chromatography (eluting with 2 % methanol in dichi orom ethane) to afford methyl l-(6-methylpyrazin-2-yl)piperidine-4- carboxylate 53-4 (750 rng, 3.19 mmol, 62 99% yield) as brown solid. LC MS: ES+ 235.9.

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

Reference:
Patent; C4 THERAPEUTICS, INC.; VEITS, Gesine, Kerstin; HE, Minsheng; HENDERSON, James, A.; NASVESCHUK, Christopher, G.; PHILLIPS, Andrew, J.; GOOD, Andrew, Charles; (471 pag.)WO2019/191112; (2019); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 914452-71-4, 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 914452-71-4 as follows.

To a solution of 2-bromo-6-methylpyrazine (3 g, 17.3 mmol) in carbon tetrachloride (30 ml) were added at r.t. under an argon atmosphere N-bromo succinimide (3.39 g, 19.1 mmol) and benzoyl peroxide (420 mg, 1.73 mmol). The mixture was stirred for 24 fir, while a 75 W lamp was shining on the orange reaction mixture). The mixture was filtered, washed with CC14 and concentrated. The residue was dissolved in EtOAc, washed with sat aq NaHC03, brine, dried over MgS04, filtered and concentrated. The crude product was purified by silica gel chromatography using a heptane/EtOAc gradient as eluent, providing the title compound (1.88g, 43%) as brown solid.

According to the analysis of related databases, 914452-71-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; FLOHR, Alexander; GROEBKE ZBINDEN, Katrin; KOERNER, Matthias; LERNER, Christian; WO2013/178569; (2013); 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. 914452-71-4, name is 2-Bromo-6-methylpyrazine, A new synthetic method of this compound is introduced below., Computed Properties of C5H5BrN2

Pd2(dba)3 (38.4 mg, 0.042 mmol), DavePhos (33.0 mg, 0.084 mmol) and sodium tert-butoxide (60.4 mg, 0.629 mmol) were all placed in a 2 mL microwave vial. To this was added 2-bromo-6- methylpyrazine (81 mg, 0.469 mmol), followed by rac- I -((2S,3R,4R)-4-amino-2-cyclopropyl-3-methyl-3,4-dihydroquinolin-1(2H)-yl)ethanone (for a preparation see Intermediate 14, 51.2 mg, 0.210 mmol) in I ,4-dioxane (2 mL). The mixture was heated at 120 C for 40 mm in a microwave heater. The reaction mixture was passed through a 2.5 g celite cartridge and washed through with 3 CVs of ethyl acetate. The solution was evaporated in vacuo to afford a deep orange oil. The crude product was taken up in dichloromethane and purified on a silica cartridge (25 g) by flash columnchromatography, eluting with 30% – 70% ethyl acetate in cyclohexane. The appropriate fractions were collected and concentrated in vacuo to afford a yellow solid (40.6 mg).LCMS (2 mm Formic): Rt = 0.91mm, [MH] = 337.

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; GLAXOSMITHKLINE INTELLECTUAL PROPERTY (NO.2) LIMITED; AMANS, Dominique; ATKINSON, Stephen John; HARRISON, Lee Andrew; HIRST, David Jonathan; LAW, Robert Peter; LINDON, Matthew; PRESTON, Alexander; SEAL, Jonathan Thomas; WELLAWAY, Christopher Roland; WO2014/140076; (2014); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 914452-71-4,Some common heterocyclic compound, 914452-71-4, name is 2-Bromo-6-methylpyrazine, molecular formula is C5H5BrN2, 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.

To the stirred solution of 2-bromo-6-methyl-pyrazine 51-3 (812 11 mg, 4.69 mmol) and methyl J – chloro-4-methyl-piperidine-4-carboxylate 51-2 (1000 mg, 5.16 mmol) in toluene (25 mL) was added cesium carbonate (4.59 g, 14.08 mmol). The reaction was degassed with argon for 10 minutes. Xanthphos (135 80 mg, 234.70 umoi) and Pd2(dba)3 (214 92 mg, 234.70 umoi) were added to the reaction mixture and the reaction mixture was heated at 90C for 16 hours. Reaction mixture was cooled to room temperature and diluted with ethyl acetate and water. Layers were separated and the organic layer was washed with water and brine, dried over sodium sulfate and concentrated under reduced pressure. The crude material was purified by combiflash chromatography (eluting at 2 % methanol in di chi or om ethane) to afford methyl 4-methyl- 1 -(6- methylpyrazin-2-yl)piperi dine-4-carboxyl ate 51-4 (630 mg, 2.53 mmol, 53.83% yield) as brown gum. LC MS: ES+ 250.3.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Bromo-6-methylpyrazine, its application will become more common.

Reference:
Patent; C4 THERAPEUTICS, INC.; VEITS, Gesine, Kerstin; HE, Minsheng; HENDERSON, James, A.; NASVESCHUK, Christopher, G.; PHILLIPS, Andrew, J.; GOOD, Andrew, Charles; (471 pag.)WO2019/191112; (2019); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 914452-71-4, The chemical industry reduces the impact on the environment during synthesis 914452-71-4, name is 2-Bromo-6-methylpyrazine, I believe this compound will play a more active role in future production and life.

To a solution of 2-bromo-6-methyl-pyrazine (3.10 g, 17.92 mmol, 1.00 eq) and TRIISOPROPYL BORATE (4.04 g, 21.50 mmol, 4.93 mL, 1.20 eq) in THF (30.00 mL) was added n-BuLi (2.5 M in n-hexane, 7.88 mL, 1.10 eq) dropwise at -100 C. The mixture was stirred at -100 C for 1 hour. TLC indicated reactant 1 was consumed completely and many new spots formed. The crude product hydroxylithium;(6-methylpyrazin-2-yl)boronic acid (2.90 g, crude) in THF (30 mL) was used into the next step without further purification. 0.5 mL of the mixture was quenched by MeOH (3 mL) and confirmed by HNMR. 1H MR (400MHz, D20) 8.26 (s, 1H), 7.98 (s, 1H), 2.30 (s, 3H) 1H MR (400MHz, D20) delta = 8.26 (s, 1H), 7.98 (s, 1H), 2.30 (s, 3H).

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, 2-Bromo-6-methylpyrazine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; THE GLOBAL ALLIANCE FOR TB DRUG DEVELOPMENT, INC.; KANEKO, Takushi; FOTOUHI, Nader; (68 pag.)WO2018/67762; (2018); A2;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application of 914452-71-4, 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. 914452-71-4, name is 2-Bromo-6-methylpyrazine, This compound has unique chemical properties. The synthetic route is as follows.

To a solution of 2-bromo-6-methyl-pyrazine (3.0 g, 17.31 mmol) in CCl4 (25 mL) was added NBS (4.60 g, 26.01 mmol) and AIBN (0.248 g, 1.734 mmol) at RT. The mixture was stirred at 55 C. for 48 h. H2O was added followed by extraction with EtOAc (3*100 mL). The combined organics were washed with brine, dried (Na2SO4) and concentrated in vacuo. The residue was purified over silica eluting with 5% EtOAc:Hexane to obtain i (1.40 g, 32%). 1H NMR (CDCl3, 400 MHz): delta 8.64 (s, 1H), 8.62 (s, 1H) and 4.50 (s, 2H).

The chemical industry reduces the impact on the environment during synthesis 2-Bromo-6-methylpyrazine. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Biota Europe Ltd.; Lunniss, Christopher James; Palmer, James T.; Pitt, Gary Robert William; Davies, David; Axford, Lorraine Claire; US2013/252938; (2013); 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. 914452-71-4, name is 2-Bromo-6-methylpyrazine, A new synthetic method of this compound is introduced below., Computed Properties of C5H5BrN2

To a solution of 2-bromo-6-methyl-pyrazine (300 mg, 1.7 mmol), hexamethylditin (0.45 mL, 2.1 mmol), and tetrakis(triphenylphosphine) (142 mg, 0.123 mmol) in 1,4-dioxane 8.0 mL was purged with N2 for 5 min. The reaction mixture was stirred at 100 C for 1 8h. The reaction was filtered through celite. The crude product was used in next step. MS (ESI) m/z: 259.1.

The synthetic route of 914452-71-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; DO, Steven; HU, Huiyong; KOLESNIKOV, Aleksandr; TSUI, Vickie, H.; WANG, Xiaojing; WO2014/1377; (2014); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application of 914452-71-4, A common heterocyclic compound, 914452-71-4, name is 2-Bromo-6-methylpyrazine, molecular formula is C5H5BrN2, 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.

General procedure: To a stirred solution of 1 (100mg, 577.99mumol), 2 (168mg, 924.79mumol) in DMF:water (5mL, 1:1), it was added Na2CO3 (141 mg, 1.33 mmol) and 1 mg of PdNP at room temperature. The resulting reaction mixture was heated at 100 C for 15 min, after completion of reaction reaction mass was cooled to room temperature, diluted with H2O (10 mL) and extracted with EtOAc (3×15 mL). The combined organic layer was washed with brine solution, dried over Na2SO4, filtered and concentrated under reduced pressure to afford crude compound, which was triturated with pet ether to delivered 3 (120 mg, 90%) as off-white solid. 1H NMR (500 MHz, CDCl3) delta: 8.79 (d, J = 5.0 Hz, 1H), 8.34 (d, J = 5.0 Hz, 1H), 7.70 – 7.51 (m, 1H), 7.04 – 6.92 (m, 1H), 4.09 – 3.89 (m, 2H), 2.66 – 2.59 (m, 1H); 13C NMR (126 MHz, CDCl3) delta 153.01, 151.40, 150.56, 149.51, 141.92, 138.57, 129.50, 119.66, 111.23, 109.83, 56.02, 56.01, 21.76; LC-MS (ESI): 231.16 (M+H).

The synthetic route of 914452-71-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Bendre, Ameya D.; Kodam, Kisan M.; Patil, Viraj P.; Terdale, Santosh S.; Waghmode, Suresh B.; Journal of Organometallic Chemistry; vol. 909; (2020);,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 914452-71-4, name is 2-Bromo-6-methylpyrazine, 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 914452-71-4, category: Pyrazines

General procedure: To a solution of Example 4A (50 mg, 0.176 mmol) in dioxane (0.8 mL) were added tris(dibenzylideneacetone)dipalladium(0) (Pd2(dba)3, 8.0 mg, 8.78 mumol), xantphos (10.2 mg, 0.018 mmol) and 2-chloro-3-methylpyrazine (24.8 mg, 0.193 mmol). Then potassium carbonate (72.8 mg, 0.527 mmol) was added. The reaction mixture was stirred overnight at 80 C. The reaction mixture was filtered, and the solids were washed with acetonitrile (3 ¡Á 2 mL). The filtrate and washes were concentrated under reduced pressure, and the residue was purified by preparative HPLC (Phenomenex Luna C8(2) 5 mum 100A AXIA column (30 mm ¡Á 75 mm); a gradient of acetonitrile (A) and 0.1% trifluoroacetic acid in water (B) was used, at a flow rate of 50 mL/minute (0-1.0 minute 5% A, 1.0-8.5 minutes linear gradient 5-100% A, 8.5- 11.5 minutes 100% A, 11.5-12.0 minutes linear gradient 95-5% A) to give the title compound (50 mg, 0.13 mmol, 76% yield). The reaction and purification conditions described in Example 579 substituting 2- bromo-6-methylpyrazine (33.4 mg, 0.193 mmol) for 2-chloro-3-methylpyrazine (24.8 mg, 0.193 mmol) gave the title compound. 1H NMR (501 MHz, DMSO-d6) delta ppm 8.73 (s, 1H), 7.72 (s, 1H), 7.63 (s, 1H), 7.60 (s, 1H), 7.50 (t, J = 8.9 Hz, 1H), 7.08 (dd, J = 11.4, 2.8 Hz, 1H), 6.86 (ddd, J = 8.9, 2.9, 1.2 Hz, 1H), 4.50 (s, 2H), 2.33 (s, 6H), 2.27 (s, 3H); MS (ESI+) m/z 377 (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.

Reference:
Patent; CALICO LIFE SCIENCES; ABBVIE, INC.; SIDRAUSKI, Carmela; PLIUSCHEV, Marina; FROST, Jennifer, M.; BLACK, Lawrence, A.; XU, Xiangdong; SWEIS, Ramzi, Farah; SHI, Lei; ZHANG, Qinwei, I.; TONG, Yunsong; HUTCHINS, Charles, W.; CHUNG, Seungwon; DART, Michael, J.; (661 pag.)WO2017/193063; (2017); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 914452-71-4, 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 914452-71-4 as follows.

To a solution of 2-chloro-4-phenoxypyrrolo[2,1-J][1,2,4]triazine (100 mg, 0.407 mmol), 2-bromo-6-methylpyrazine (70.4 mg, 0.407 mmol) and hexamethylditin (0.084mL, 0.407 mmol) in 1,4-dioxane (7 mL) was added tetrakis(triphenylphosphine)palladium(0) (47.0 mg, 0.041 mmol). The reaction mixture was degassed with argon and was stirred at 100 C for 18 h. The solvent was removed under reduced pressure to get a brown solid. The crude residue was purified by silica gel chromatography (ethyl acetate:Petroleum ether, 10/90) to obtain 2-(6-methylpyrazin-2-yl)-4-phenoxypyrrolo[2,1-J][1,2,4]triazine (85 mg, 0.280 mmol, 68.8 % yield). LCMS m/z 304.4 (M+H); rt 1.45 mm; Conditions B.

According to the analysis of related databases, 914452-71-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; HARIKRISHNAN, Lalgudi S.; FINK, Brian E.; BORZILLERI, Robert M.; TONUKUNURU, Gopikishan; RAHAMAN, Hasibur; WARRIER, Jayakumar Sankara; SESHADRI, Balaji; (411 pag.)WO2017/15425; (2017); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem