Category: Pyrazines

Application of 186534-02-1,Some common heterocyclic compound, 186534-02-1, name is 3,5,6-Trimethylpyrazine-2-carbaldehyde, molecular formula is C8H10N2O, 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: New a, b-unsaturated carbonyl-based compounds (5a-g and 6au)were synthesized using direct coupling technique [40] (Scheme 1). The reaction was carried out using base-catalyzed Claisen-Schmidt condensation reaction, by reacting different types of ketoneswith appropriate aromatic aldehyde at molar ratio 2:1 tosynthesize new compounds (5a-g) and at molar ratio 1:1 for (6a-u).For synthesis of 6a-u first 5a-g intermediates were synthesized andin second step appropriate aldehydes were reacted with intermediates.The detailed method of synthesis has already beenreported by us previously [38,40]. Scheme 1 shows the highlights ofsynthesis of compound 3, 4 and a, b-unsaturated carbonyl-basedcompounds along with oxime derivatives. 15 mL ethanol wastaken in a round bottom flask and aromatic aldehyde (20 mmol, 2equivalent) and specific ketone (10 mmol,1 equivalent) were addedand dissolved using a stirrer for 2-3 min at 5 C. Into the abovesolution, 40% NaOH solution in ethanol was added drop wise andthe mixture was stirred for 1-24 h at 27 C. The color change andprecipitate formation in the reaction mixture showed productformation. TLC was used to monitor the reaction and acidified icewas added to quench the reaction once completed. The isolation ofcompounds was done by recrystallization and/or by using columnchromatography.

The synthetic route of 186534-02-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Zha, Gao-Feng; Qin, Hua-Li; Youssif, Bahaa G.M.; Amjad, Muhammad Wahab; Raja, Maria Abdul Ghafoor; Abdelazeem, Ahmed H.; Bukhari, Syed Nasir Abbas; European Journal of Medicinal Chemistry; vol. 135; (2017); p. 34 – 48;,
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Reference of 63286-28-2, The chemical industry reduces the impact on the environment during synthesis 63286-28-2, name is 2-Chloro-3-hydrazinylpyrazine, I believe this compound will play a more active role in future production and life.

General procedure: To a well-stirred solution of I 2 (0.2 mmol)TBHP (2 mmol,70% in water) K2CO3 (1 mmol) in 1,4-dioxane (10 mL) were added benzaldehyde 1a (1 mmol) and 2-hydrazinopyridine 2a (1 mmol), and then the reaction mixture was stirred at 60 C. After completion of the raction as indicated by TLC (1 h), the reaction mixture was cooled to room temperature. Then the reaction mixture was treated with 10 % Na2S2O3 (20 mL) and extracted with ethyl acetate (10 mL¡Á3). The combined organic layer was dried over anhydrous Na2SO4 and concentrated under reduced pressure. The crude product was purified through silica gel column chromatography using a mixture of EtOAc and petroleum ether as eluent to afford the targeted product in 72-97 % 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-Chloro-3-hydrazinylpyrazine, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Wu, Yachuang; Yang, Yifeng; Qi, Yinliang; Du, Shimei; Zhang, Yongsheng; Ding, Liang; Zhao, Yanfang; Tetrahedron Letters; vol. 59; 48; (2018); p. 4216 – 4220;,
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Pyrazine | C4H4N2 – PubChem

Synthetic Route of 14508-49-7, 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. 14508-49-7, name is 2-Chloropyrazine, This compound has unique chemical properties. The synthetic route is as follows.

1)Will be 31.3 grams(80 wt%, 50 mmol)Hydrazine hydrate was added to 100 ml three-necked flask,Heating up to 60 ,Under magnetic stirring, 11.5 g was slowly added dropwise(100 mmol)2-chloropyrazine,The reaction was carried out at a temperature of 60 C for 10 hours,After completion of the reaction, the mixture was cooled to 2 C,Precipitation of solids,filter,Dried to afford 6.63 g of a white solid,Yield 60.5%;

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

Reference:
Patent; Nankai University; Wang, Baolei; Li, Zhengming; Zhang, Yan; (13 pag.)CN106749262; (2017); A;,
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Pyrazine | C4H4N2 – PubChem

Application of 957344-74-0, The chemical industry reduces the impact on the environment during synthesis 957344-74-0, name is 5,8-Dibromoimidazo[1,2-a]pyrazine, I believe this compound will play a more active role in future production and life.

Step 3 (5-Bromoimidazo[l,2-a]pyrazin-8-yl)-(4-(4-methylpiperazin-l-yl)phenylamine[00292] 4-(4-Methylpiperazin-lyl)phenylamine (5 08g, 26 6mmol) and NN- diisopropylethylamine (4 6mL, 26 6mmol) and 5,8-dibromoimidazo[l,2-a]pyrazine (6 Ig, 22 2mmol) in iso-propanol (15OmL), is heated at 900C for 2 days The solvent is removed in vacuo, and the crude residue partitioned between DCM and IN NaOH The organic phase is separated, then washed with water followed by brine. The organic layer is separated, dried (MgSO4) and evaporated. The crude residue is chromatographed on silica gel, eluting with DCM followed by 96:4 DCM NH 3 (7M in MeOH), and the fractions containing the desired product are combined and evaporated The residue is t?turated with Et2theta to afford the title compound as a 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, 5,8-Dibromoimidazo[1,2-a]pyrazine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; GALAPAGOS N.V.; WO2007/131991; (2007); A1;,
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Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 36070-75-4, name is 5-Chloropyrazine-2-carbonitrile, 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 36070-75-4, Recommanded Product: 5-Chloropyrazine-2-carbonitrile

Step 1: Synthesis of 5-(4-fluoro-lH-pyrazol-l-yl)pyrazine-2-carbonitrile. (0362) To a solution of 5-chloropyrazine-2-carbonitrile (280 mg, 2.0 mmol) in DMF was added 4-fluoro-lH-pyrazole (170 mg, 2.0 mmol) and potassium acetate (395 mg, 4.0 mmol). The mixture was stirred at 100 C for 4 hours, then cooled to 20 C, poured into brine (25 mL), and extracted with ethyl acetate. The organic layer was dried over sodium sulfate, concentrated, and purified by column chromatography (hexane: ethyl acetate = 5: 1) to give 5-(4-fluoro-lH- pyrazol-l-yl)pyrazine-2-carbonitrile (310 mg, 82%). The structure was confirmed by LC-MS.

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Reference:
Patent; BLUEPRINT MEDICINES CORPORATION; BRUBAKER, Jason, D.; KIM, Joseph, L.; WILSON, Kevin, J.; WILSON, Douglas; DIPIETRO, Lucian, V.; (84 pag.)WO2017/79140; (2017); A1;,
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Pyrazine | C4H4N2 – PubChem

Related Products of 54608-52-5, These common heterocyclic compound, 54608-52-5, name is 2-Hydrazinopyrazine, 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 vigorously stirred mixture of alpha-bromonitroalkane (0.50 mmol), heteroaryl hydrazine (0.60 mmol, 1.2 equiv), potassium iodide (1.0 mmol, 2.0 equiv) and potassium carbonate (1.0 mmol, 2.0 equiv) in 1,2-dimethoxyethane (5.0 mL) was added a solution of urea hydrogen peroxide in 1,2-dimethoxyethane/water (4:1) (0.50 M solution, 1.0 mL, 0.50 mmol, 1.0 equiv) over 2 h via syringe pump at r.t. After the addition was complete, the mixture was stirred for an additional 4 h. Aqueous sodium thiosulfate was then added and the mixture was extracted with ethyl acetate. The combined organic layers were washed with brine, dried over sodium sulfate, and concentrated in vacuo. The residue was purified by flash column chromatography to give pure fused triazole.

The synthetic route of 54608-52-5 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Tokumaru, Kazuyuki; Bera, Kalisankar; Johnston, Jeffrey N.; Synthesis; vol. 49; 20; (2017); p. 4670 – 4675;,
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Pyrazine | C4H4N2 – PubChem

Application of 16298-03-6,Some common heterocyclic compound, 16298-03-6, name is Methyl 2-aminopyrazine-3-carboxylate, molecular formula is C6H7N3O2, 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.

Example 3a: methyl 3-amino-6-iodopyrazine-2-carboxylate 1.5 equivalents of N-iodosuccinimide are added at room temperature to 5 g (32.7 mmol) of a methyl 3-aminopyrazine-2-carboxylate solution in 25 ml of dimethylformamide. The reaction medium is heated at 65 C for 1 hour, added together with 0.5 equivalents of N-iodosuccinimide and maintained at 65C for 24 hours. After returning to room temperature, the solvent is evaporated and then the product is extracted several times with dichloromethane. The organic phases are combined, washed with 10% sodium bisulfite solution, dried on magnesium sulfate and concentrated to yield 8 g (88%) of methyl 3-amino-6-iodopyrazine-2-carboxylate in the form of a yellow solid. LCMS (EI, m/z): (M+l) 280 1H NMR: deltaEta ppm (400 MHz, DMSO): 8.50 (1H, s, CHarom), 7.50 (2H, bs, NH2), 3.20 (3H, s, CH3).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Methyl 2-aminopyrazine-3-carboxylate, its application will become more common.

Reference:
Patent; PIERRE FABRE MEDICAMENT; SOKOLOFF, Pierre; CACHOUX, Frederic; WO2014/16433; (2014); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 622392-04-5, 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 622392-04-5 as follows.

a) 2-Bromo-5- (4- [ 1 ,2,4] triazol- 1 -yl-but- 1 -ynyl)-pyrazine A mixture of 2.00 g (7.0 mmol) 2-bromo-5-iodo-pyrazine, 1.02 g (8.4 mmol) 1- but-3-ynyl- IH-[1, 2,4] triazole, 9.95 g (98.3 mmol) triethylamine, 147 mg (0.8 mmol) copper (I) iodide and 404 mg (0.3 mmol) tetrakis(triphenylphophine) palladium (0) in 30 ml DMF were stirred at room temperature overnight. After addition of 80 ml dichloromethane and 100 ml 0.5N HCl the phases were separated and the organic layer was dried over Na2SCv Column chromatography (silica, ethyl acetaterheptane 0:1 to 1:1) returned 0.90 g (46%) 2-bromo-5-(4-[ 1,2,4] triazol- 1-yl- but-l-ynyl)-pyrazine as a yellow solid. MS: M = 278.0 (ES+) 1H-NMR (400 MHz, D.-DMSO): delta= 3.08 (t, 6.5 Hz, 2H), 4.47 (t, 6.5 Hz, 2H), 8.02 (s, IH), 8.49 (s, IH), 8.62 (s, IH), 8.82 (s, IH).

According to the analysis of related databases, 622392-04-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; WO2007/39226; (2007); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 6164-79-0, The chemical industry reduces the impact on the environment during synthesis 6164-79-0, name is Methyl 2-pyrazinecarboxylate, I believe this compound will play a more active role in future production and life.

Synthesis of pyrazin-2-ylmethanol:To a stirred solution of methyl pyrazine-2-carboxylate (0.5 g, 3.62 mmol) in H20 (10 mL) was added NaBH4 (685 g, 18.02 mmol) portion wise at 0 C, and the reaction mixture was allowed to warm to RT and stirred for 30 min under inert atmosphere. To this saturated K2C03 (10 mL) and EtOH (5 mL) was added and stirring was continued for another 1 h at RT. The progress of the reaction was monitored by TLC; the reaction mixture was extracted with EtOAc. The combined organic layer was dried over sodium sulphate, filtered and concentrated in vacuo to afford crude pyrazin-2-ylmethanol (0.3 g). LC-MS: 99.91%; 111.9 (M++l) (column; X-bridge C-18, (50×3.0 mm, 3.5mu); RT 0.72 min. 0.1% TFA in water: ACN; 0.8 ml/min); TLC: 100% EtOAc (Rf: 0.2).

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, Methyl 2-pyrazinecarboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ENVIVO PHARMACEUTICALS, INC.; RIPKA, Amy; SHAPIRO, Gideon; MCRINER, Andrew; WO2012/40230; (2012); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 1458-01-1, 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 1458-01-1 as follows.

A stirred suspension of 3,5-diamino-6-chloro-pyrazine-2-carboxylic acid methyl ester (110 g, 542.9 mmol) in MeOH (500 ml) at 5-10¡ã C. (ice-bath) is treated dropwise with a suspension of lithium hydroxide (46.6 g, benzoyl}benzoyl} mmol) in water (500 ml). The reaction mixture is heated to 50¡ã C. for 5 hours then cooled to room temperature and stirred overnight. The resulting precipitate is collected by filtration and dried in a vacuum oven to afford Lithium 3,5-diamino-6-chloro-pyrazine-2-carboxylic acid as the lithium salt (di-hydrate); [M-Li] 187.

According to the analysis of related databases, 1458-01-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Vertex Pharmaceuticals Incorporated; Van Goor, Fredrick F.; Burton, William Lawrence; US2015/231142; (2015); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem