Pyrazines

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;,
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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;,
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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;,
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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;,
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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

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

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;,
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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

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. 56423-63-3, name is 2-Bromopyrazine belongs to Pyrazines compound, it is a common compound, a new synthetic route is introduced below. Application In Synthesis of 2-Bromopyrazine

Intermediates 2(R)-N-((l S,2S)-l-(3-bromopyrazin-2-yl)-2-(2,3-difluorophenyl)hex-5- enyl)-2-methylpropane-2-sulfinamide. In an oven-dried 250 mL round-bottomed flask was dissolved diisopropylamine (1.7 mL, 12 mmol) in tetrahydrofuran (40 mL) to give a colorless solution under nitrogen. After cooling to -30C, n-BuLi (4.3 mL, 11 mmol) was added, and the mixture was briefly warmed up to rt for 3 min. After cooling down to -78C, 2-bromopyrazine (0.98 mL, 10.7 mmol) was added dropwise via syringe. The resulting yellow solution was stirred at -78C for 5 min. (R,E)-N- ((S)-2-(2,3-difluorophenyl)hex-5-enylidene)-2-methylpropane-2-sulfinamide (2.089 g, 6.67 mmol) in 4 mL anhydrous tetrahydrofuran (plus 3 mL rinse) was added via canuula, and the mixture was stirred for 2 h at -75C. The reaction was quenched with saturated sodium bicarbonate solution and diluted with ethyl acetate. The layers were separated. The aqueous layer was extracted with ethyl acetate. The combined organic layers were washed with brine, dried, and concentrated to give a tan oil. Flash column chromatography up to 80% ethyl acetate/hexane afforded the desired product (1.964 g, 62%) as a dense tan oil: XH NMR (400 MHz, CHLOROFORM-d) delta ppm 8.33 (d, J=2.26 Hz, 1 H) 8.26 (d, J=2.26 Hz, 1 H) 6.99 – 7.22 (m, 3 H) 5.74 (d, J=6.53 Hz, 1 H) 5.18 (dd, J=9.29, 5.27 Hz, 1 H) 4.85 – 4.99 (m, 2 H) 4.30 (d, J=9.54 Hz, 1 H) 3.66 – 3.77 (m, 1 H) 2.17 (br. s., 1 H) 1.80 – 2.04 (m, 3 H) 1.05 (s, 9 H); 19F NMR (376 MHz, CHLOROFORM-d) delta ppm -138.41 (d, J=15.61 Hz, 1 F) -144.20 – – 143.20 (m, 1 F); 13C NMR (101 MHz, CHLOROFORM-d) delta ppm 155.19 (s, 1 C) 151.32 – 149.72 (dd, J=13.87 and 249.47 Hz, 1 C) 150.24 – 147.67 (dd, J=12.72 and 246.95 Hz, 1 C) 142.89 (s, 1 C) 141.44 (br. s., 1 C) 140.47 (s, 1 C) 136.93 (d, J=10.02 Hz, 1 C) 127.54 (d, J=10.79 Hz, 1 C) 124.12 – 124.96 (m, 1 C) 123.41 – 123.97 (m, 1 C) 115.23 – 1 15.83 (m, 1 C) 1 15.09 (s, 1 C) 59.93 – 60.56 (m, 1 C) 56.10 – 56.69 (m, 1 C) 40.72 – 41.81 (m, 1 C) 30.81 (s, 1 C) 30.34 (br. s., 1 C) 21.94 (q, J=6.17 Hz, 3 C).

The synthetic route of 56423-63-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; LUO, Guanglin; DUBOWCHIK, Gene M.; MACOR, John E.; CHEN, Ling; WO2012/154354; (2012); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 4430-75-5, The chemical industry reduces the impact on the environment during synthesis 4430-75-5, name is Octahydro-2H-pyrido[1,2-a]pyrazine, I believe this compound will play a more active role in future production and life.

To 3-(chlorosulfonyl)benzoyl chloride (0.36 g 1.5 mmol) in anhydrous dichloromethane (50 mL) was added octahydro-lH-pyrido[l,2-alpha]pyrazine (0.21 g, 1.5 mmol) in dichloromethane (4 mL) slowly over 10 minutes at room temperature. Then sodium carbonate (0.32 g, 3 mmol) was added. The mixture was stirred at room temperature for 5 hours. Then 3 -(trifluoromethyl)aniline (2.9 g, 18 mmol) was added. The mixture was stirred at room temperature for 5 days, then sodium carbonate(0.32 g, 3 mmol) and methanol (5 mL) were added, the mixture was stirred for 20 minutes, then filtered, and concentrated. The residue was purified by chromatography on silica gel (methanol/ethyl acetate = 1 : 10) to give the titled compound: 1U NMR (400 MHz, DMSO-J6) delta ppm 1.00-1.27 (m, 3H), 1.42-2.10 (m, 7H), 2.70-3.40 (m, 4H), 4.25-4.40 (m, IH), 7.40 (m, 3H), 7.50 (m, IH), 7.70 (m, 3H), 7.85 (m, IH), 10.80 (br s, IH); MS (ESI) m/z 468 (M+H)+.

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, Octahydro-2H-pyrido[1,2-a]pyrazine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ABBOTT LABORATORIES; ZHANG, Qingwei; STEWART, Andrew, O.; XIA, Zhiren; WO2010/83264; (2010); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem