Author: Jessica.F

Reference of 89123-58-0, A common heterocyclic compound, 89123-58-0, name is 5-Bromopyrazine-2,3-diamine, molecular formula is C4H5BrN4, 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.

To a 50 mL round bottom flask fitted with a reflux condenser, under nitrogen were added 5-bromopyrazine-2,3-diamine (400 mg, 2.1 mmol) and triethyl orthoformate (3.1 g, 21.2 mmol). The mixture was heated to reflux and stirred for 24 h. The reaction was cooled to rt, concentrated to dryness and the residue purified by HPLC to give 320 mg (76% yield) of the title compound. MS (ESI): mass calcd. for C5H3BrN4, 197.95; m/z found, 199.1 [M+H]+.

The synthetic route of 89123-58-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; Eccles, Wendy; Fitzgerald, Anne E.; Hack, Michael D.; Hawryluk, Natalie A.; Jones, William M.; Keith, John M.; Krawczuk, Paul; Lebsack, Alec D.; Liu, Jing; Mani, Neelakandha S.; McClure, Kelly J.; Meduna, Steven P.; Rosen, Mark D.; US2015/252008; (2015); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 22047-25-2, name is Acetylpyrazine, 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 22047-25-2, Formula: C6H6N2O

General procedure: A 100 mL round-bottom flask charged with 2-acetylpyrazine (1.47 g, 2 mmol) was added MeOH (30 mL), KOH pellets (0.675 g,2 mmol) and water (2 mL). The resulting mixture was stirred for10 min and then added corresponding n,n?-dimethoxybenzaldehydes (1.0 g, 1 mmol) and ammonium solution (6 mL) was added slowly stirring at room temperature for 4 h, a white precipitate obtained was filtered, washed with MeOH and diethyl ether. The crude products on recrystallization in a mixture of CHCl3:MeOH (1:1) gave white crystals of desired compounds, 1-4. 2,2?-[4-(2,3-dimethyoxyphenyl)pyridine-2,6-diyl]dipyrazine(1): Yield: 65%; M.P.: 212 C; 1H NMR (400 MHz, CDCl3, delta ppm): 3.737 (s, 3H, OCH3), 3.945 (s, 3H, OCH3), 7.041e7.045 (d, 1H, ArHC4),7.114e7.119 (d, 1H, ArHC6), 7.134e7.165 (t, 1H, ArHC5), 8.635-8.650(t, 4H, pz, HAA’5,6), 8.683 (s, 2H, pz, HAA’3), 9.869-9.871 (s, 2H, py,HB3,5); 13C{1H} NMR (100 MHz, CDCl3, delta ppm): 153.84 (C2,6 of py),151.02 (C4 of py), 148.73 (C3,30 of pz), 144.58 (C6,60 of pz), 143.57(C5,50 of pz), 133.59 (C6 of ph), 122.11 (C1 of ph), 122.04 (C3,5 of py),110.77 (C5 of ph), 101.31 (C3 of ph), 61.06 (OCH3), 55.08 (OCH3); FTIR (KBr disc, nu cm-1): 2965 (w), 1739 (s), 1588 (m), 1465 (s), 1415(m), 1365 (s), 1270 (s), 1220 (m), 1109 (s), 1053 (s), 1003 (s), 852 (s),786 (s).

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:
Article; Golla, Ramesh; Kumar, P. Raghavendra; Suchethan; Foro, Sabine; Nagaraju; Journal of Molecular Structure; vol. 1201; (2020);,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 1435953-98-2, name is 5-Methoxy-3-methylpyrazin-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 1435953-98-2, category: Pyrazines

l,l’-Thiocarbonyldiimidazole (226 mg, 1.21 mmol) and then hydrochloric acid in dioxane (0.55 mL, 2.2 mmol, 4 mol/L) were added to a solution of 5-methoxy-3-methyl-pyrazin-2-amine (153 mg, 1.10 mmol) in DCM (5.5 mL) under air. The reaction was stirred at r.t. for 4 hours, filtered and the solid washed with DCM (2 x 10 mL). The filtrate was concentrated in vacuo and purified by flash column chromatography on silica (gradient elution with 0% to 100% EtOAc in isohexanes) to give the title compound (127 mg, 40 % Yield). A few drops of isobutylamine were added to the LCMS sample of the product before analysis LCMS [M+H]+ 255, RT 1.46 minutes [M = l-isobutyl-3-(5-methoxy-3- methyl-pyrazin-2-yl)thiourea] (Method 4).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 5-Methoxy-3-methylpyrazin-2-amine, and friends who are interested can also refer to it.

Reference:
Patent; UCB BIOPHARMA SRL; CHOVATIA, Prafulkumar Tulshibhai; CONNELLY, Rickki Lee; FRANKLIN, Richard Jeremy; HASLETT, Gregory William; HENRY, Alistair James; MADDEN, James; NEUSS, Judi Charlotte; NORMAN, Timothy John; PHILPS, Oliver; PITT, William Ross; RAMPALAKOS, Konstantinos; SELBY, Matthew Duncan; SELVARATNAM, Suganthan; TRANI, Giancarlo; ZHU, Zhaoning; (768 pag.)WO2019/243550; (2019); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Related Products of 68774-77-6, 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. 68774-77-6 name is 8-Chloro[1,2,4]triazolo[4,3-a]pyrazine, 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.

General procedure: A mixture of chloro compound (50 mg) and amine derivative (2 equiv.) in PEG 400 (2 mL) wasstirred at 120 C for 5 min. After completion the reaction was then cooled to room temperature. DCM and water were added and the phases were separated. The aqueous phase was extracted withDCM and the organic phase was dried and filtered. The removal of solvent gave the product as solid.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 8-Chloro[1,2,4]triazolo[4,3-a]pyrazine, and friends who are interested can also refer to it.

Reference:
Article; Campos, Joana F.; Loubidi, Mohammed; Scherrmann, Marie-Christine; Berteina-Raboin, Sabine; Molecules; vol. 23; 3; (2018);,
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. 20737-42-2, name is 3-Oxo-3,4-dihydropyrazine-2-carboxylic acid, A new synthetic method of this compound is introduced below., Product Details of 20737-42-2

EXAMPLE 67 3-Hydroxypyrazine-2-carboxylic acid is converted to the methyl ester and the ester is reduced with lithium aluminium hydride in tetrahydrofuran to give 3-hydroxy-2-hydroxymethylpyrazine.

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; Smith Kline & French Laboratories Limited; US3950333; (1976); A;,
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. 1196152-38-1, name is 2-Bromo-5-(trifluoromethyl)pyrazine, A new synthetic method of this compound is introduced below., name: 2-Bromo-5-(trifluoromethyl)pyrazine

To a suspension of N-(3-aminobicyclo[l . l . l]pentan-l-yl)-2-(3,4- dichlorophenoxy)acetamide hydrochloride (0.08 g, 0.237 mmol, Example 2B) in N,N- dimethylformamide (0.5 mL, 6.46 mmol) was added N,N-diisopropylethylamine (0.166 mL, 0.948 mmol) followed by 2-bromo-5-(trifluoromethyl)pyrazine (0.065 g, 0.284 mmol). The reaction mixture was stirred overnight at 90 C. It was then concentrate under reduced pressure at 50 C. The residue was purified by flash column chromatography on silica gel (24 g) eluted with heptane and ethyl acetate (0 to 100%) to give 40 mg of the title compound (35.9% yield) as a white solid. JH NMR (400 MHz, DMSO-<) delta ppm 8.78 (s, 1H), 8.59 (s, 1H), 8.44 (s, 1H), 7.99 (s, 1H), 7.55 (d, J = 8.8 Hz, 1H), 7.27 (d, J = 2.8 Hz, 1H), 6.99 (dd, J = 9.0, 2.9 Hz, 1H), 4.51 (s, 2H), 2.37 (s, 6H). 19F NMR (376 MHz, DMSO-<) delta ppm -64.83; MS (ESI+) mJz 447 (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; CALICO LIFE SCIENCES LLC; ABBVIE INC.; MARTIN, Kathleen, Ann; SIDRAUSKI, Carmela; FROST, Jennifer, M.; PLIUSHCHEV, Marina, A.; TONG, Yunsong; BLACK, Lawrence, A.; XU, Xiangdong; SHI, Lei; ZHANG, Qingwei, I.; CHUNG, Seungwon; SWEIS, Ramzi, Farah; DART, Michael, J.; RANDOLPH, John, T.; MURAUSKI, Kathleen; (674 pag.)WO2019/90076; (2019); 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. 19847-12-2, name is Pyrazinecarbonitrile, A new synthetic method of this compound is introduced below., Computed Properties of C5H3N3

Pyrazine-2-carbonitrile (10.5 g, 100 mmol) was dissolved in PhMe (100 mL) at 0 C. and 4-chlorophenyl magnesium bromide (100 ml, 1.0 M in Et2O, 100 mmol) was added portion-wise over 5 min. The reaction mixture was stirred for 6 h and NaBH4 (7.58 g, 201 mmol) and tBuOH (100 mL) were added. The reaction mixture was warmed to 60 C. for 18 h and quenched with 1 M aq NaOH solution. The aqueous layer was extracted with EtOAc and the combined organic layers were dried (MgSO4) and concentrated in vacuo. The residue was purified by flash chromatography (DCM:EtOH:NH3 200:8:1 to 50:8:1) to give the title compound as a brown oil (7.46 g, 34%). MS (ESI+) m/z=220.0 (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; PROXIMAGEN LIMITED; Evans, David; Carley, Allison; Stewart, Alison; Higginbottom, Michael; Savory, Edward; Simpson, Iain; Nilsson, Marianne; Haraldsson, Martin; Nordling, Erik; Koolmeister, Tobias; US2013/102587; (2013); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 25710-18-3, The chemical industry reduces the impact on the environment during synthesis 25710-18-3, name is 2,3-Dichloropyrido[2,3-b]pyrazine, I believe this compound will play a more active role in future production and life.

To a stirred solution of 4.5 g of compound 3 (22.5 mmol) in 10 mL of acetonitrile, 2.5 mL of phenylacetylene (23.0 mmol), 25 mL of triethylamine (TEA; 180 mmol), 500 mg of palladium(II) acetate (2.2 mmol), 419 mg of copper iodide (2.2 mmol), and 577 mg of triphenylphosphine (2.2mmol) were added, and the mixture was heated up to 80 ¡ãC for 3 h. The resulting mixture was concentrated, dried under vacuum, and extracted with a mixture of EtOAc and water.The organic layer was separated, washed with water, and dried over MgSO4. After the removal of the solvent by a rotary evaporator, the residue was purified by column chromatography using (EtOAc: n-hexane = 1:4) to achieve compound 4 as a yellow solid with 68percent yield

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, 2,3-Dichloropyrido[2,3-b]pyrazine, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Park, Jeong Hoon; Kim, Heejung; Kim, Dong-Yeon; Yang, Seung Dae; Hur, Min Goo; Kim, Sang Wook; Yu, Kook Hyun; Bulletin of the Korean Chemical Society; vol. 36; 7; (2015); p. 1778 – 1783;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 4949-13-7, 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 4949-13-7 as follows.

[0211] To a mixture of 4-(Aminomethyl)benzonitrile hydrochloride (1.6 g, 9.3 mmol, 1.0 equiv) and IPA (15.0 mL) in a microwave vial (20 mL) were added 2-fluoropyrazine (1.0 g, 10.2 mmol, 1.1 equiv) and DIPEA (2.9 g, 22.2 mmol, 2.4 equiv). The vial was sealed and heated at 170 C in a microwave reactor for 4 h, concentrated onto 10 g of silica, and purified by silica gel chromatography (80 g column, 0-10% MeOH in DCM) to provide 1.2 g (62%) of 4-((pyrazin-2-ylamino)methyl)benzonitrile as a pale yellow solid. LRMS (ES) m/z 211.2 (M+H). 1H-NMR (Methanol-^, 400 MHz, ppm) d 7.96 – 7.90 (m, 2H), 7.70 – 7.62 (m, 3H), 7.53 – 7.48 (m, 2H), 4.63 (s, 2H).

According to the analysis of related databases, 4949-13-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; CYTOKINETICS, INC.; MORGAN, Bradley P.; VANDERWAL, Mark; CHUANG, Chihyuan; (0 pag.)WO2020/5888; (2020); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 98-97-5, name is Pyrazine-2-carboxylic acid, 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 98-97-5, COA of Formula: C5H4N2O2

To a solution containing 2-pyrazine carboxylic acid (10 g, 80.5 mmol) in dichloromethane (150 mL) was added 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride EDC (18.5 g, 96.6 mmol) and 1-hydroxybenzotriazole HOBT (13.05 g, 96.6 mmol) and the resulting solution stirred at 25 C. for 30 minutes. Then 1-cyclohexylglycine methyl ester (16.7 g, 80.5 mmol) and Hunig’s base (31.24 g, 241 mmol) was added and the reaction mixture stirred for 2 hours. The reaction mixture was partitioned between water and dichloromethane. The organic layer was removed and dried over MgSO4, filtered and concentrated in vacuo and purified via flash chromatography using ethyl acetate/hexane (20/80 to 30/70) to give a foam (13.3 g, 60%). The product of the previous reaction (6.54 g, 24 mmol) was dissolved in ethanol and treated with 1N sodium hydroxide (35.4 mL, 35.3 mmol) at 25 C. for 4 hours. The mixture was neutralized with 10% HCl to pH 4 and extracted with dichloromethane. The organic layer was removed and dried over MgSO4, filtered and concentrated in vacuo to afford a foam (5 g, 81%).

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

Reference:
Patent; Abbott Laboratories; US2010/29686; (2010); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem