Pyrazines

Adding a certain compound to certain chemical reactions, such as: 87486-34-8, name is 3,5-Dibromo-1-methylpyrazin-2(1H)-one, 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 87486-34-8, Product Details of 87486-34-8

Example 186a 5-Bromo-1-methyl-3-(pyridin-3-ylamino)pyrazin-2(1H)-one 186a A 100-mL single-neck round-bottomed flask equipped with a magnetic stirrer and a reflux condenser was charged with pyridin-3-amine (940 mg, 10 mmol), 3,5-dibromo-1-methylpyrazin-2(1H)-one (5.4 g, 20 mmol), i-propanol (50 mL), and di-i-propylethylamine (10 mL). The mixture was heated at reflux for 5 h. After the completion of the reaction, it was cooled to room temperature. The solvent was removed under reduced pressure. The crude was purified by silica-gel column chromatography eluting with 30:1 dichloromethane/methanol to afford 186a (1.4 g, 50percent) as a yellow solid. MS-ESI: [M+H]+ 281.6.

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Reference:
Patent; F.Hoffmann-La Roche AG; CRAWFORD, James John; ORTWINE, Daniel Fred; WEI, BinQing; YOUNG, Wendy B.; EP2773638; (2015); B1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application 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.

In the hydrothermal reaction kettle are respectively added with 2, 6 – two chlorine pyrrole qin (10.0 g, 67.1 mmol) and ammonia (100 ml), 100 C lower reaction 5 h. The completion of the reaction, cooling to room temperature, filtered, the filter cake is hexane (16 ml) beating shall 2 – amino -6 – chloropyrazine white solid 8.2 g, yield is 95.0%.

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; Guizhou University; Zhou Zhixu; Li Fei; Yue Yi; (7 pag.)CN107857737; (2018); A;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

These common heterocyclic compound, 1458-18-0, name is Methyl 3-amino-5,6-dichloropyrazine-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. HPLC of Formula: C6H5Cl2N3O2

Examples 54 and 55222.03 140.57[0266] Methyl 3-amino-5,6-dichloro-2-pyrazinecarboxylate, (3.2 gm, 0.0144 moles) and benzoyl chloride (7.03 gm, 0.05 moles) are combined in chloroform (50 mL) and pyridine (8 mL) is added. This mixture is stirred at 50C overnight. Additional portions of benzoyl chloride (3.5.0 gm, 0.025 moles) and pyridine (4 mL) are added and heating is continued at 65C overnight. The solution is cooled and methanol (25 mL) is added. After stirring for 30 minutes, the solvents are removed under reduced pressure. The solid residue is recrystallized from n-butanol.

The synthetic route of Methyl 3-amino-5,6-dichloropyrazine-2-carboxylate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JANUS BIOTHERAPEUTICS, INC.; LIPFORD, Grayson, B.; ZEPP, Charles, M.; WO2012/167046; (2012); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 939412-86-9, 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. 939412-86-9, name is (3-Chloropyrazin-2-yl)methanamine hydrochloride belongs to pyrazines compound, it is a common compound, a new synthetic route is introduced below.

A mixture of SM (1.4 g, crude, 7.8 mmol), (3-chloropyrazin-2-yl)methanamine hydrochloride (1.4 g, 7.8 mmol), HATU (2.7 mg, 7.8 mmol) and TEA (3.2 mg, 31.2 mmol) in DCM (30 mL) was stirred at 25C overnight. The mixture was quenched with H20 (60 mL) and it was extracted with DCM (25 mL X 3). The combined organic layers were dried over anhydrous sodium sulfate, filtered and concentrated to give a crude product. The crude product was purified by prep- TLC to give 1 (1.3 g, 50 %). LCMS: m/z = 309 [M+H]+.

The synthetic route of (3-Chloropyrazin-2-yl)methanamine hydrochloride has been constantly updated, and we look forward to future research findings.

Reference:
Patent; LIAO, Xibin; SUZHOU BAIJIBUGONG PHARMACEUTICAL TECHNOLOGY CO. LTD.; LI, Jia; LU, Zhijian; ZHOU, Yubo; GAO, Anhui; (100 pag.)WO2018/175512; (2018); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

These common heterocyclic compound, 6863-73-6, name is 3-Chloropyrazin-2-amine, 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. Recommanded Product: 6863-73-6

8-Chloroimidazor 1 ,2-alpyrazine[00237] 2-Bromo-l,l-diethoxyethane (6.21 mL, 0.041 mmol) was added to a mixture of 48% HBr (aq.) solution (1.64 mL) and water (20 mL) and the resulting mixture was stirred under reflux for 1 hour. The reaction mixture was then allowed to cool and washed with brine (2 x 30 mL), dried (MgSO4) and carefully concentrated in vacuo. The resulting oil was dissolved in 1 ,2-dimethoxoethane (20 mL) and added to a suspension of 2-amino-3 -chloro- pyrazine (2.142 g, 0.016 mmol) in 1 ,2-dimethoxoethane (30 mL). 48 % HBr (aq.) solution (0.313 mL) was then added and the resulting mixture was stirred under reflux for 1 hour. Upon cooling a precipitate formed which was collected by filtration and washed with diethyl ether to give the crude HBr salt. This was dissolved in NaHCO3 (aq.) and extracted into DCM. Drying of the organic layer (MgSO4) followed by concentration in vacuo provided the title compound (1.9 g, 75%) as a yellow/pale brown solid. 1H NMR (d6-DMSO): 8.68-8.64 (IH, br m), 8.30-8.26 (IH, br m), 7.88-7.85 (IH, br m), 7.75-7.70 (IH, br m).

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

Reference:
Patent; BioMarin IGA, Ltd.; WREN, Stephen Paul; WYNNE, Graham Michael; LECCI, Cristina; WILSON, Francis Xavier; PRICE, Paul Damien; MIDDLETON, Penny; WO2010/69684; (2010); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application of 486424-37-7, These common heterocyclic compound, 486424-37-7, name is 3-Amino-6-bromopyrazine-2-carboxylic acid, 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.

A suspension of S-amino-beta-bromo-pyrazine^-carboxylic acid (0.5g, 2.3 mmol) and 3-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-phenylboronic acid (patent WO 2003076422, 1.28g, 4.6 mmol) in MeCN (20ml) was treated with K2CO3 (3.8g, 27.5 mmol) in H2O (5ml) under nitrogen at room temperature. The mixture was stirred for 10 min before adding bis(triphenylphosphine)palladium dichloride (0.08g, catalytic) and stirred at 9O0C for 3 hr. The cooled reaction mixture was dilute with H2O (20ml), basified to ph4, filtered to remove catalyst and evaporated. The residue dissolved in DCM (200ml), washed with brine, dried (MgSO4) and condensed. The solid residue was subjected to flash column chromatography on silica eluting gradient of hexane to (2:1 , v/v) ethyl acetate and hexane to give title compound (0.38g, 44%) as a yellow solid; LC/MS: Rt 2.78 (Method A) [M+H]+ 374.

The synthetic route of 486424-37-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; VERNALIS (R & D) LIMITED; WO2008/38010; (2008); 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. 356783-15-8, name is 3,6-Dichloropyrazine-2-carboxylic acid, A new synthetic method of this compound is introduced below., Recommanded Product: 3,6-Dichloropyrazine-2-carboxylic acid

(b) In 2.0 mL of methylene chloride was suspended 0.2 g of 3,6-dichloro-2-pyrazinecarboxylic acid. Then, 0.001 mL of N,N-dimethylformamide and 0.14 mL of oxalyl chloride were successively added at an ice-cooled temperature, and the mixture thus formed was stirred at room temperature for 40 minutes. The reaction mixture was concentrated to dryness under reduced pressure and then dissolved in 3.0 mL of acetonitrile. Then, 0.3 g of potassium fluoride and 0.056 g of 18-crown-6-ether were added and the mixture thus formed was stirred at 60 C. for 2.5 hours in an atmosphere of nitrogen gas. The reaction mixture was poured into 3.0 mL of methanol, the insoluble matter was filtered off, and then the filtrate was concentrated to dryness under reduced pressure. The residue was purified by silica gel chromatography [eluent: n-hexane:ethyl acetate-9:1] to obtain 0.15 g of methyl 3,6-difluoro-2-pyrazinecarboxylate as a colorless oily product.

The synthetic route of 356783-15-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Toyama Chemical Co., Ltd.; US2003/130213; (2003); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 313340-08-8,Some common heterocyclic compound, 313340-08-8, name is 3,5-Dichloro-6-ethylpyrazine-2-carboxamide, molecular formula is C7H7Cl2N3O, 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.

Preparation Example 210 A mixture of 3,5-dichloro-6-ethylpyrazine-2-carboxamide (500 mg), 5-methyl-6-(4-methylpiperazin-1-yl)pyridin-3-amine (470 mg), diisopropylethylamine (800 muL), and dioxane (10 mL) was stirred in a microwave reaction device at 150 C. for 30 minutes. After leaving to be cooled, water was added thereto, and the precipitated solid was collected by filtration and then dried under reduced pressure to obtain 5-chloro-6-ethyl-3-{[5-methyl-6-(4-methylpiperazin-1-yl)pyridin-3-yl]amino}pyrazine-2-carboxamide (210 mg) as a yellow solid.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3,5-Dichloro-6-ethylpyrazine-2-carboxamide, its application will become more common.

Reference:
Patent; ASTELLAS PHARMA INC.; Matsuya, Takahiro; Kondoh, Yutaka; Shimada, Itsuro; Kikuchi, Shigetoshi; Iida, Maiko; Onda, Kenichi; Fukudome, Hiroki; Takemoto, Yukihiro; Shindou, Nobuaki; Sakagami, Hideki; Hamaguchi, Hisao; US2014/323463; (2014); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application of 16298-03-6, 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 16298-03-6 as follows.

Step 1a: Methyl 3-[(2,4-dimethoxybenzyl)amino]pyrazine-2-carboxylate Sodium triacetoxyborohydride (7.82 g, 36.89 mmol) was added to a mixture of methyl 3-aminopyrazine-2-carboxylate (4.00 g, 26.12 mmol) and 2,4-dimethoxybenzaldehyde (4.83 g, 29.04 mmol) in 1,2-dichloroethane (90 ml). The reaction was continued at room temperature for 24 hours. Sodium triacetoxyborohydride (13.0 g, 61.34 mmol) and 2,4-dimethoxybenzaldehyde (8.0 g, 48.14 mmol) were added and the reaction continued at room temperature over night. Water and DCM were added and the phases separated. The product was purified further by flash chromatography (SiO2, heptane:ethyl acetate, product came at 50percent ethyl acetate) and recrystallisation (DCM/heptane) to give a slightly yellow solid (5.00 g, 63percent). 1H NMR (400 MHz, CDCl3) delta 8.35-8.27 (br, 1H), 8.22 (d, 1H), 7.82 (d, 1H), 7.20 (d, 1H), 6.48-6.43 (m, 1H), 6.43-6.37 (m, 1H), 4.63 (d, 2H), 3.93 (s, 3H), 3.84 (s, 3H), 3.77 (s, 3H). MS m/z 304 (M+H)+.

According to the analysis of related databases, 16298-03-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Cheng, Leifeng; Jonforsen, Maria; Schell, Peter; US2009/88439; (2009); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 76537-18-3, A common heterocyclic compound, 76537-18-3, name is 3-Bromo-5-chloropyrazin-2-amine, molecular formula is C4H3BrClN3, 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.

3-Bromo-5-chloropyrazin-2-amine (200 mg, 0.96 mmol),Triethylamine (290 mg, 2.88 mmol), cuprous iodide(5mg, 0.33mmol)And bis(triphenylphosphine)palladium dichloride (13 mg, 0.02 mmol) was dissolved in tetrahydrofuran (5 mL).The reaction solution was stirred at room temperature.Then trimethylethynyl silicon (0.15 mL, 1.06 mmol)Slowly adding dropwise to the above reaction solution,After completion of the dropwise addition, the resulting reaction solution was heated to 55 C to continue the reaction for 1 hour.After the reaction system is cooled to room temperature,The reaction solution was diluted with ethyl acetate (50 mL).Filter and concentrate the filtrate under reduced pressure.The residue obtained was purified by silica gel column chromatography (PE/EA (v/v) = 30/1).The title compound was obtained as a pale yellow solid ( 208 g, 96%).

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; Guangdong Dongyangguang Pharmaceutical Co., Ltd.; Ren Qingyun; Tang Changhua; Yin Junjun; Yi Kai; Lei Yibo; Wang Yejun; Zhang Yingjun; Nie Biao; Xu Juan; Yan Huan; Chen Jianping; (90 pag.)CN108727369; (2018); A;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem