Category: Pyrazines

Adding a certain compound to certain chemical reactions, such as: 143591-61-1, name is 3-Bromo-8-chloroimidazo[1,2-a]pyrazine, 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 143591-61-1, Quality Control of 3-Bromo-8-chloroimidazo[1,2-a]pyrazine

Ammonia of a 30% (w/v) aqueous solution (2.3 mL, 57.37 mmol)was added to a solution of 3-bromo-8-chloroimidazo [1,2-a]pyrazine(500 mg, 2.15 mmol) in acetonitrile in a microwave-adaptedvial. The reaction was submitted to microwave irradiations during2 h at 140 C. The solvent is removed under reduced pressure. Thecrude mixture was dissolved in ethyl acetate and successivelywashed with saturated aqueous chloride ammonium, distilledwater and finally brine. The organic phase was dried on sodiumsulphate, filtered and concentrated under reduced pressure. Thecompound is obtained as a white solid (87% yield). C6H5BrN4. Mw:213.03 g/mol. Mp 242-243 C. 1H-RMN delta (ppm, 400 MHz, DMSOd6)7.10 (s, 2H, NH), 7.36 (d, 1H, CH 6, J = 8 Hz), 7.56 (d, 1H, CH 7,J = 8 Hz), 7.65 (s, 1H, CH 2). 13C-RMN delta (ppm, 100 MHz, DMSO-d6)97.81 (Cq 1), 108.03 (CH 7), 130.19 (CH 6), 132.45 (CH 2), 133.46 (Cq30), 150.72 (Cq 4). MS (ESI+ , QTof, m/z): 213.1 [M+H]+. HRMScalculated for C6H6BrN4 212.9776, found 212.9785.

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; Patinote, Cindy; Bou Karroum, Nour; Moarbess, Georges; Deleuze-Masquefa, Carine; Hadj-Kaddour, Kamel; Cuq, Pierre; Diab-Assaf, Mona; Kassab, Issam; Bonnet, Pierre-Antoine; European Journal of Medicinal Chemistry; vol. 138; (2017); p. 909 – 919;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Related Products of 58138-79-7,Some common heterocyclic compound, 58138-79-7, name is 2,6-Diiodopyrazine, molecular formula is C4H2I2N2, 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.

A mixture of 2,6-diiodopyrazine (1 g, 3.013 mmol), tert-butyl (2S)-2-isobutylpiperazine- 1-carboxylate (949.3 mg, 3.917 mmol) and K2CO3 (624.7 mg, 4.520 mmol) in DMF (5 mL) was heated to 900C and stirred for 17 hrs. It was then allowed to cool and diluted with ethyl acetate and water, further washed organic layer with water and brine, dried (MgSO4) and concentrated to give an orange oil. It was then columned on silica gel eluting with 1 : 1 EtOAc/hexanes to give (S)-tert-buty 4-(6-iodopyrazin-2-yl)-2-isobutylpiperazine-l-carboxylate as a yellow oil 1.05 g, 78%). ES+ 447. IHNMR (CDCl3) 0.98 (6H, d), 1.23 – 1.45 (2H, m), 1.55 – 1.63 (I H, m), 2.91 – 3.00 (I H, m), 3.03 – 3.21 (2H, m), 3.98 – 4.20 (3H, m), 4.25 (I H, brs), 7.95 (I H, s), 8.06 (I H, s).

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

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; JIMENEZ, Juan-Miguel; STUDLEY, John; WO2010/11772; (2010); A2;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Related Products of 1458-01-1, These common heterocyclic compound, 1458-01-1, name is Methyl 3,5-diamino-6-chloropyrazine-2-carboxylate, 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: Methyl 3,5-diamino-6-chloropyrazine-2-carboxylate 2 (1 eq.) was combined with K2CO3 (10 eq.), the appropriate (het)aryl boronic acid (1.5 eq.) and Pd(PPh3)4 (5 mol%) in a two-neck round bottom flask. The flask was connected to a condenser and purged with nitrogen. A 4:1 mixture of anhydrous toluene: MeOH (60 mL) was added via syringe and the reaction mixture was heated at reflux for 0.5-18 h. The mixture was allowed to cool to room temperature and filtered through Celite (10 x 3 cm, eluting with 3 x 20 mL EtOAc). The filtrate was evaporated to dryness and the residue purified by silica gel flash column chromatography using EtOAc/pet spirit.

The synthetic route of 1458-01-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Buckley, Benjamin J.; Majed, Hiwa; Aboelela, Ashraf; Minaei, Elahe; Jiang, Longguang; Fildes, Karen; Cheung, Chen-Yi; Johnson, Darren; Bachovchin, Daniel; Cook, Gregory M.; Huang, Mingdong; Ranson, Marie; Kelso, Michael J.; Bioorganic and Medicinal Chemistry Letters; vol. 29; 24; (2019);,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 14508-49-7, name is 2-Chloropyrazine, 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 14508-49-7, COA of Formula: C4H3ClN2

General procedure: A mixture of 2-chloropyrazine (1mmol), 4-ethylphenylboronic acid or 4-methoxy-phenyl boronic acid (1.5mmol), K2CO3 (3mmol), Pd(OAc)2 (0.03mmol), water (2mL) and ethanol (6mL) was stirred at 90C in air for 24h. The reaction mixture was extracted with ethyl acetate, then the combined organic layers were washed with water, dried over MgSO4, filtered, and the solvent was removed on a rotary evaporator. The products were isolated by flash chromatography on silica gel with CH2Cl2 as eluent. The characterization data for 1: Yield: 87%. 1H NMR (400MHz, CDCl3): delta 8.99 (s, 1H), 8.57 (s, 1H), 8.44 (s, 1H), 7.92 (d, J=8.0Hz, 2H), 7.31 (d, J=8.0Hz, 2H), 2.69 (q, J=7.6Hz, 2H), 1.25 (t, J=7.6Hz, 3H). 13C NMR (100MHz, CDCl3): delta 152.8, 146.4, 144.1, 142.6, 142.0, 133.8, 128.6, 126.9, 28.7, 15.4. MS (EI, 70eV) m/z=185.1 (M+H)+. Elemental analysis calcd (%) for C12H12N2: C 78.23, H 6.57, N 15.21. Found: C 78.46, H 6.31, N 15.33. The characterization data for 2, see Supporting Information.

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-Chloropyrazine, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Xu, Chen; Wang, Zhi-Qiang; Fu, Wei-Jun; Ji, Bao-Ming; Yuan, Xiao-Er; Han, Xin; Xiao, Zhi-Qiang; Hao, Xin-Qi; Song, Mao-Ping; Journal of Organometallic Chemistry; vol. 777; (2015); p. 1 – 5;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application of 4774-14-5, 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. 4774-14-5, name is 2,6-Dichloropyrazine belongs to Pyrazines compound, it is a common compound, a new synthetic route is introduced below.

To a solution of diisopropylamine (13.0 niL, 92.6 mmol, 2.3 eq.) in anhydrousTHF (300 rnL) at -78C under N2 was added dropwise a solution of 1.6 M nBuLi in hexanes (57.9 rnL, 92.6 mmol, 2.3 eq.). After 1 hour a solution of 2,6-dichloropyrazine in anhydrous THF (6.0 g, 40.3 mmol) was added dropwise over 30 minutes. After stirring at -78C for 1 hour, the reaction mixture was poured onto crushed dry ice (solid carbon dioxide), and the reaction mixture was stirred at ambient temperature for 16 hours. The mixture was then diluted with water (100 mL) and washed with ethyl acetate (3 x 100 mL). The aqueous layer was cooled to 00C, acidified with 2N HCl until pH ~ 2, and extracted with ethyl acetate (3 x 100 mL). The combined organic extracts were dried (Na2SO4), filtered and evaporated in vacuo. The resultant crude was purified by column chromatography (Si-PPC, gradient 0% to 50%, methanol in dichloromethane) to give the desired product as a beige solid (3.16 g, 40.6 %). 1H NMR (CDCl3, 400MHz) delta ppm 8.60 (s, IH).

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

Reference:
Patent; GENENTECH, INC.; WO2009/85983; (2009); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

136927-64-5, name is 1-Chloropyrrolo[1,2-a]pyrazine, belongs to Pyrazines compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. Computed Properties of C7H5ClN2

To a stirred solution of 1-chloro-pyrrolo[1 ,2-a]pyrazine (1.53g, 10 mmol) in THF (90 ml.) was added at 0 C a solution of 1 ,3-dibromo-5,5-dimethylhydantoin (1.49g, 4.9mmol) in THF (10 ml_), via dropping funnel. The funnel was washed with a little THF and this added to the reaction mixture. The reaction mixture was stirred for an hour at 0 C, diluted with DCM and washed with saturated sodium bicarbonate solution. The aqueous layer was back-extracted with DCM. The organic extracts were passed through a hydrophobic frit and evaporated. The residue was purified on silica eluting with 8% EtOAc in iso- hexane to give the title compound as a white solid (1.54 g, 67 %). (0617) [00321] 1 H NMR (CDCI3 ppm) d 7.8 (dd, 1 H, J = 5, 1 Hz), 7.5 (d, 1 H J = 5 Hz ), 7.0 (0618) (dd, 1 H, J = 4, 1 Hz), 6.9 (d 1 H, J = 4Hz). LCMS (m/z) [M+H] 231 , 233

The synthetic route of 136927-64-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; THE UNIVERSITY COURT OF THE UNIVERSITY OF EDINBURGH; WALKINSHAW, Malcolm D.; PETTIT, Simon Neil; HIGHTON, Adrian; MCNAE, Iain William; (117 pag.)WO2019/106368; (2019); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Related Products of 55557-52-3, 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. 55557-52-3, name is 3-Chloropyrazine-2-carbonitrile belongs to Pyrazines compound, it is a common compound, a new synthetic route is introduced below.

3-chloropyrazine-2-carbonitrile (32 g) was dissolved in 300 ml of acetic acid and 14 g of Raney nickel in 50% slurry,Slowly add to the above solution, pass 4.5 bar of hydrogen, and stir overnight at room temperature.Filtered through diatomaceous earth, and the filtrate was spin-dried. The ethyl acetate was taken with water to obtain a solid. The solid was dissolved in 50 C ethyl acetate.A hydrogen chloride gas was passed into the ethyl acetate solution, and a solid was precipitated, filtered, and the filter cake was washed with ethyl acetate.Drying under vacuum at 50 C gave 23 g (3-chloropyrazin-2-yl) methylamine.hydrochloride.

The synthetic route of 3-Chloropyrazine-2-carbonitrile has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Andikang (Wuxi) Biological Technology Co., Ltd.; Zhu Xiaoyun; Jiang Weiping; (34 pag.)CN110563733; (2019); A;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 36070-80-1, The chemical industry reduces the impact on the environment during synthesis 36070-80-1, name is 5-Chloropyrazine-2-carboxylic acid, I believe this compound will play a more active role in future production and life.

To a suspension of 5-chloropyrazine-2-carboxylic acid (3.00 g, 18.92 mmol) in Dichloromethane (35 mL) and DMF (0.15 mL) at rt was added oxalyl chloride (2.411 mL, 21.76 mmol) dropwise over 10 mm. The mixture was stirred at rt for 2 h before it was concentrated under vacuum to dryness. The residue was dissolved in dichloromethan (35 mL). dimethylamine in THF (11.83 mL, 23.65 mmol) was was added at rt over 10mm, followed by the addition of triethylamine (5.80 mL, 41.6 mmol). The mixture was stirred at rt for 3 h. The mixture was diluted with ethyl acetate (50 mL) and filtered through Celite. The filtrate was concentrated under vacuum to dryness, and the residue was applied to ISCO (220 g silica gel, solid loading, 70-100% ethyl acetate) to provide the desired product, 5-chloro-N,N-dimethylpyrazine-2-carboxamide (3.18 g, 17.13 mmol,91 % yield), as a white solid.

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, 5-Chloropyrazine-2-carboxylic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; LIU, Chunjian; LIN, James; MOSLIN, Ryan M.; WEINSTEIN, David S.; TOKARSKI, John S.; WO2015/89143; (2015); 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. 875781-43-4, name is 2-Bromo-5H-pyrrolo[2,3-b]pyrazine, A new synthetic method of this compound is introduced below., Quality Control of 2-Bromo-5H-pyrrolo[2,3-b]pyrazine

General procedure: 2-Bromo-5H-pyrrolo[3,2-b]pyrazine(4; 0.471 g,2.39 mmol), 4-pyridylboronic acid (0.58 g, 4.72 mmol), dichloro 1,1′-bis(diphenylphosphino)ferrocenepalladium (II) dichloromethane adduct (0.097 g, 0.12 mmol), acetonitrile(3 mL) and 1M sodium carbonate (3 mL) were placed in a 10 mL CEM microwavevial. The vial was capped and irradiated in a CEM microwave reactor for 30minutes at 150 C.Water (3 mL) and ethyl acetate (9 mL) were added the layers were partitioned. Theaqueous layer was extracted with ethyl acetate (2 x 10 mL). The combined organicextracts were washed with saturated sodium chloride (5 mL), dried over MgSO4and concentrated under reduced pressure. The residue was purified by preparativereverse phase HPLC to give 2-(pyridin-4-yl)-5H-pyrrolo[2,3-b]pyrazine(14; 0.28 g,60%) as an off white solid: 1H NMR (400 MHz, DMSO-d6) delta 12.24 (s, 1H), 9.00(s, 1H), 8.69 (dd, J = 4.5, 1.6 Hz, 2H), 8.12 (dd, J = 4.5, 1.6Hz, 2H), 7.98 (d, J = 3.6 Hz, 1H), 6.74 (d, J = 3.6 Hz, 1H); ESMSm/z 197.1 (M+1).

The synthetic route of 875781-43-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Burdick, Daniel J.; Wang, Shumei; Heise, Christopher; Pan, Borlan; Drummond, Jake; Yin, Jianping; Goeser, Lauren; Magnuson, Steven; Blaney, Jeff; Moffat, John; Wang, Weiru; Chen, Huifen; Bioorganic and Medicinal Chemistry Letters; vol. 25; 21; (2015); p. 4728 – 4732;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 4774-14-5, 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. 4774-14-5, name is 2,6-Dichloropyrazine, This compound has unique chemical properties. The synthetic route is as follows.

A solution of 2,6-dichloropyrazine (15kg, 1O1.4mol, 1.00 equiv) in water(20 L), ammonia water (25 L, 25 %) was placed in a 100 L pressure tank reactor. The resulting solution was stirred for 6 h at 120C. The reaction progress was monitored by TLC (EA:PE = 1 : 1) until the starting material was consumed, and cooled to room temperature. Thesolids were collected by filtration. The solid was washed with water and dried. The solidwas washed with petroleum ether to remove the unreacted starting materials. The product (7.8kg, purity = 95 %, 60% yield) was obtained as a white solid.

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

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; CUI, Haifeng; HENNESSY, Alan; JIN, Qi; MILES, Timothy James; MOSS, Stephen Frederick; PEARSON, Neil David; (173 pag.)WO2017/29602; (2017); A2;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem