Pyrazines

75907-74-3, name is (3,5,6-Trimethylpyrazin-2-yl)methanol, 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 C8H12N2O

Reaction step 2-hydroxymethyl-3,5,6-trimethylpyrazine (9.5 g, 62.5 mmol) was sequentially added to a 250 mL three-necked flask,MnO2 (16.2 g, 187.5 mmol),Ethanol 100mL,Reflux 12h,TLC (petroleum ether – ethyl acetate 2: 1) detection reaction is almost complete,cool down,Filtering to obtain filtrate,Ethanol recovery under reduced pressure,To give a yellow solid,Purification by silica gel column chromatography (petroleum ether-ethyl acetate 4: 1)3,5,6-trimethylpyrazine-2-carbaldehyde as a pale yellow solid,The yield was 93.9%

The synthetic route of 75907-74-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Anhui University of Chinese Medicine; Li, Jiaming; He, Guangwei; Chu, Zhaoxing; Huang, Weijun; Zhang, Yanchun; Xie, Di; Zuo, Jian; Liu, Huicai; (11 pag.)CN105237487; (2016); A;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 768-05-8, name is Pyrazinoic acid hydrazide, 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 768-05-8, category: Pyrazines

To a suspension of 4-[(2-chloro-4-fluorophenyl)carbonyl]-2-piperazinone (I3)(O.78 g, 3.04 mmol) in Dichloromethane (DCM) (7.60 ml) was added triethyloxonium tetrafluoroborate (0.606 g, 3.19 mmol) and the mixture was stirred at room temperature under argon. After 5-10 minutes it turned to a yellow solution. TLC showed the formation of the imidate (some unreacted starting material always present due to instability of imidate on TLC). After 1 hour 2-pyrazinecarbohydrazide (0.504 g, 3.65 mmol, commercially available) was added but it was insoluble. After 15 minutes the solvent was evaporated in vacuo and the residue taken in n-butanol (7.60 ml) and heated at reflux (120 0C). After 2 hours LCMS showed a main peak which is consistent with the desired product. It was concentrated in vacuo and the residue was purified by flash chromatography (Biotage SP4, 40 + M cartridge) with a gradient of 2M ammonia in MeOH 0 to 10% in DCM. The crude product was then dissolved in EtOAc (50 mL), the precipitate filtered off (50 mg of impurity by LCMS) and the solution washed with sat. NH4CI (3OmL), water (30 mL) and brine (30 mL) and finally dried over MgSO4 to afford an off-white solid that was fruther purified by MDAP to isolate the desired product in 310 mg as a white solid.LC/MS: (M+H)+= 359, retention time = 0.74 minutes (2 minutes run). 1H NMR (500 MHz; d6-DMSO) delta 9.37 (1 H, d), 8.74 (2H, m), 7.65 (1 H, m), 7.63 (1 H, dd), 7.37 (1 H, td), 5.28 (1 H, d), 4.94 (1 H, d), 4.43 (2H, m), 3.67 (2H, m).

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:
Patent; GLAXO GROUP LIMITED; DEAN, David Kenneth; MUNOZ-MURIEDAS, Jorge; SIME, Mairi; STEADMAN, Jon Graham Anthony; THEWLIS, Rachel Elizabeth Anne; TRANI, Giancarlo; WALTER, Daryl Simon; WO2010/125102; (2010); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 1209646-17-2,Some common heterocyclic compound, 1209646-17-2, name is 5-(4-(tert-Butoxycarbonyl)piperazin-1-yl)pyrazine-2-carboxylic acid, molecular formula is C14H20N4O4, 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 suspension of 1-77 (3.0 g, 9.71 mmol) in THF (40 ml) is added 1,1′- carbonyldiimidazole (1.6 g, 9.71 mmol) at room temperature. The mixture is stirred at 50 C for 30 minutes. After this time 1-16 (2.5 g, 8.83 mmol) is added and the resulting mixture is heated at 80C for 3 hours. The mixture is cooled down and treated with AcOH (8ml). The mixture is warmed to 80C and stirred over night. Upon cooling toroom temperature, the reaction is concentrated and diluted with water. The product is extracted into DCM (2x). The combined organics are washed with brine and dried over anhydrous MgS04. The mixture is filtered and concentrated. The remaining crude is purified via flash chromatography (silica gel, 0-5% MeOH/DCM) to afford 1-78 (2.2 g).

The synthetic route of 1209646-17-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; BARTOLOZZI, Alessandra; BOSANAC, Todd; CHEN, Zhidong; DE LOMBAERT, Stephane; HUBER, John; LO, Ho Yin; LOKE, Pui Leng; LIU, Weimin; MORWICK, Tina Marie; OLAGUE, Alan; RIETHER, Doris; TYE, Heather; WU, Lifen; ZINDELL, Renee; WO2012/24150; (2012); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 6863-74-7, 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. 6863-74-7, name is 6-Chloropyrazine-2-carbonitrile belongs to pyrazines compound, it is a common compound, a new synthetic route is introduced below.

Reference Example 105 2-Cyano-6-dimethylaminopyrazine 2-Chloro-6-cyanopyrazine (0.85 g, 6.09 mmol) and 1.67 N dimethylamine in acetonitrile (4.00 ml, 6.70 mmol) were added to THF (100 ml), and the mixture was stirred at room temperature for 2 hrs.. The reaction mixture was combined with ethyl acetate and water.. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate.. The solvent was evaporated to give the titled compound (0.50 g, 55 %) as pale yellow crystals.1H-NMR (CDCl3) delta: 3.16 (6H, s), 8.07 (1H, s), 8.18 (1H, s). IR(KBr): 2233, 1738, 1680, 1591, 1521, 1367, 1242, 1150, 993, 846 cm-1.

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

Reference:
Patent; Takeda Chemical Industries, Ltd.; EP1424336; (2004); 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. 55557-52-3, name is 3-Chloropyrazine-2-carbonitrile, A new synthetic method of this compound is introduced below., Safety of 3-Chloropyrazine-2-carbonitrile

The starting compound 3-chloropyrazine-2-carboxamide was prepared via partial hydrolysis of the nitrile group of 3-chloropyrazine-2-carbonitrile (Fluorochem, Co., Hadfield, Derbyshire, UK). A mixture of concentrated (30%) hydrogen peroxide (29 mL) and water (195 mL) was prepared and alkalinized with an 8% (w/v) solution of sodium hydroxide to obtain a solution with pH 9. The carbonitrile (104 mmol) was then added portionwise into the heated (50 C) mixture over a period of 30 min. The whole mass was stirred for an additional 2.5 h at 55 C while the pH was periodically monitored and alternatively adjusted to the value of 9 by adding a few drops of 8% NaOH solution. The reaction mixture was cooled in a fridge to initiate crystallization. The crude product was recrystallized from ethanol [27]. The yield of this reaction was approximately 80%.

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:
Article; Jandourek, Ondrej; Tauchman, Marek; Paterova, Pavla; Konecna, Klara; Navratilova, Lucie; Kubicek, Vladimir; Holas, Ondrej; Zitko, Jan; Dolezal, Martin; Molecules; vol. 22; 2; (2017);,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 59489-71-3, 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. 59489-71-3, name is 2-Amino-5-bromopyrazine, This compound has unique chemical properties. The synthetic route is as follows.

Example 54 2 (R)- (3-CHLORO-4-METHANESULFONYL-PHENYL)-3-CYCLOPENTYL-N- [5- (L (S), 2-dihydroxy- ethyl)-pyrazin-2-yl]-propionamide [000276] This compound was prepared through a linear synthesis (Method A) and a convergent synthesis (Method B). Method A: [000277] A solution of 2-amino-5-bromopyrazine (500 mg, 2.87 mmol) in N, N- dimethylformamide (15 ML) was treated with tetrakis (triphenylphosphine) palladium (0) (66 mg, 0.06 MMOL), N, N-DIISOPROPYLETHYL AMINE (1.25 mL, 7.18 mmol), lithium chloride (426 mg, 0.06 mmol), and vinyltri-n-butyltin (840 L, 2.87 mmol), and the reaction was heated at 120C for 4 h. After such time, the reaction was cooled to 25C, treated with a saturated aqueous potassium fluoride solution (10 mL), and stirred at 25C overnight for 16 h. The solution was then diluted with methylene chloride (25 ML) and extracted with methylene chloride (3 x 15 mL). The combined organic layers were dried over sodium sulfate, filtered, and concentrated in vacuo. Biotage chromatography (FLASH 40S, Silica, 40/60 to 20/80 HEXANES/ETHYL acetate) afforded 2-amino-5-vinylpyrazine (211 mg, 61%) as a light yellow solid: EI-HRMS m/e calcd for C6H7N3 (M+) 121.0640, found 121.0642.

The chemical industry reduces the impact on the environment during synthesis 2-Amino-5-bromopyrazine. I believe this compound will play a more active role in future production and life.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; WO2004/52869; (2004); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 5521-55-1, These common heterocyclic compound, 5521-55-1, name is 5-Methylpyrazine-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.

5-methylpyrazine acid (about 0.27 mmol, prepared as Example 2), EDCI (0.35mmol) and DMAP (0.027mmol) were dissolved in dry methylene chloride (20mL), The chlorinated hederagenin(152 mg, 0.27 mmol, prepared as Example 4) was then dissolved in dichloromethane (20 ml). It was dropped into 5-methylpyrazine acid solution within 20 minutes, and stirred at room temperature for 12 hours. Then diluted with dichloromethane (20mL), washed with saturated aqueous NaCl solution, It was dried over anhydrous sodium sulfate, concentrated and purified by column chromatography to obtain a white powder, H-21. Yield: 40% (afterchromatograph with DCM / MeOH, 1% -2%) as a white powder, m.p .: 175.8 C.

The synthetic route of 5521-55-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Xinhuo Zhiyao (Beijing) Technology Co., Ltd.; Fang Kang; Guo Wenbo; Wang Penglong; Cheng Gang; (26 pag.)CN110964078; (2020); A;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application of 313340-08-8, These common heterocyclic compound, 313340-08-8, name is 3,5-Dichloro-6-ethylpyrazine-2-carboxamide, 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 solution of compound6(0.4 mmol) and anappropriateaniline derivatives(0.2 mmol) in 1,4-dioxane, was added DIPEA (0.4 mmol). The mixture was stirred at 100oC for 12 h. The solution was diluted withwater, andfiltered. The residue was washed with water twice and dried to give the crude product as yellow solid in 42-74% yield.

Statistics shows that 3,5-Dichloro-6-ethylpyrazine-2-carboxamide is playing an increasingly important role. we look forward to future research findings about 313340-08-8.

Reference:
Article; Wang, Yueliang; Xing, Li; Ji, Yinchun; Ye, Jiqing; Dai, Yang; Gu, Wangting; Ai, Jing; Song, Zilan; Bioorganic and Medicinal Chemistry Letters; vol. 29; 6; (2019); p. 836 – 838;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

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. 27825-21-4, name is Methyl 3-chloropyrazine-2-carboxylate, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C6H5ClN2O2

EXAMPLE II-23 In 15 mL of acetonitrile was dissolved 0.3 g of methyl 3-chloro-2-pyrazinecarboxylate. At an ice-cooled temperature, 10% fluorine gas (a fluorine gas diluted with nitrogen gas) was introduced at a rate of 45 ml per minute for a period of 18 minutes. Then, while elevating the temperature from the ice-cooled temperature to room temperature, nitrogen gas was introduced for one hour, and the reaction product was concentrated under reduced pressure. The oily product thus obtained was purified by silica gel column chromatography (eluent: n-hexane:ethyl acetate=10:1] to obtain 0.03 g of methyl 3-chloro-6-fluoro-2-pyrazinecarboxylate as a colorless oily product. IR (neat) cm-1: 1736 1H-NMR (CDCl3) delta: 4.04(3H,s), 8.43(1H,d,J=8.3 Hz)

According to the analysis of related databases, 27825-21-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Toyama Chemical Co., Ltd.; US2003/130213; (2003); 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. 313340-08-8, name is 3,5-Dichloro-6-ethylpyrazine-2-carboxamide, A new synthetic method of this compound is introduced below., Application In Synthesis of 3,5-Dichloro-6-ethylpyrazine-2-carboxamide

A mixture of 3,5-dichloro-6-ethylpyrazine-2-carboxamide (3a,503 mg, 2.29 mmol), 2-methoxy-4-[4-(4-methylpiperazin-1-yl)piperidin-1-yl]aniline (699 mg, 2.30 mmol), DIPEA (0.78 mL, 4.56 mmol) and 1,4-dioxane (10 mL) was stirred at 110 C for 25 h. After the mixture was cooled to room temperature, saturated aqueous NaHCO3 solution was added, and the resulting slurry was extracted with CHCl3. The organic layer was washed with brine, dried over anhydrous MgSO4, and concentrated in vacuo. The residue was purified by silica gel column chromatography (CHCl3/MeOH/28% aqueous NH3=100:0:0 to90:9:1). The resulting product was washed with EtOAc, filtered and dried in vacuo at 50 C to give 9 (701 mg, 63%) as an orange solid. 1HNMR (DMSO-d6): delta 1.25 (3H, t, J=7.4 Hz), 1.43-1.59 (2H, m),1.77-1.91 (2H, m), 2.14 (3H, s), 2.20-2.72 (11H, m), 2.79 (2H, q,J=7.5 Hz), 3.64-3.75 (2H, m), 3.85 (3H, s), 6.51 (1H, dd, J=2.4, 8.8 Hz), 6.65 (1H, d, J=2.4 Hz), 7.83 (1H, d, J=1.6 Hz), 8.04 (1H, d,J=8.8 Hz), 8.12 (1H, d, J=1.6 Hz), 11.11 (1H, s); MS (ESI) m/z[M+H]+ 488.

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:
Article; Iikubo, Kazuhiko; Kurosawa, Kazuo; Matsuya, Takahiro; Kondoh, Yutaka; Kamikawa, Akio; Moritomo, Ayako; Iwai, Yoshinori; Tomiyama, Hiroshi; Shimada, Itsuro; Bioorganic and Medicinal Chemistry; vol. 27; 8; (2019); p. 1683 – 1692;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem