Pyrazines

Application of 75907-74-3,Some common heterocyclic compound, 75907-74-3, name is (3,5,6-Trimethylpyrazin-2-yl)methanol, molecular formula is C8H12N2O, 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 3,5,6-trimethylpyrazine-2-yl)methanol (see Bioorg. Med. Chem. 2007, 15, 3315; 14.8 g, 97.2 mmol) and manganes(IV) oxide (30.0 g) in dichloromethane was stirred at room temperature for 3 days. The reaction mixture was filtrated through Celite with dichloromethane. The filtrate was combined and concentrated in vacuo to give 3,5,6-trimethylpyrazine-2-carbardehyde. MS (APCI): m/z 151 (M+H).

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

Reference:
Patent; MITSUBISHI TANABE PHARMA CORPORATION; KAWANISHI, Eiji; HONGU, Mitsuya; TANAKA, Yoshihito; WO2011/105628; (2011); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Some common heterocyclic compound, 33332-25-1, name is Methyl 5-chloropyrazine-2-carboxylate, molecular formula is C6H5ClN2O2, 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: Methyl 5-chloropyrazine-2-carboxylate

Example 190C methyl 5-ethenylpyrazine-2-carboxylate (1430) A solution of methyl 5-chloropyrazine-2-carboxylate (3 g, 17.38 mmol), potassium vinyltrifluoroborate (5.12 g, 38.2 mmol) and 1,1?-bis(diphenylphosphino)ferrocenedichloro palladium(II) dichloromethane complex (1.272 g, 1.738 mmol) in isopropyl alcohol (45 mL, anhydrous) was treated with triethylamine (4.85 mL, 34.8 mmol) and the atmosphere was vacuum purged with N2 a few times. The mixture was heated at 80 C. under N2 for 2 hours and cooled. The mixture was partitoned between saturated aqueous NaHCO3 solution (50 mL) and ethyl acetate (150 mL). The layers were separated and the aqueous layer was extracted with ethyl acetate (2×50 mL). The combined ethyl acetate layers were washed with brine, dried (MgSO4), filtered, and concentrated. The residue was chromatographed on silica gel eluting with a gradient of 25 to 100% ethyl acetate in heptanes to provide the title compound (2.28 g, 13.89 mmol, 80% yield)1H NMR (400 MHz, CDCl3) delta 9.23 (d, J=1.0 Hz, 1H), 8.67 (d, J=1.1 Hz, 1H), 6.89 (dd, J=17.4, 10.8 Hz, 1H), 6.51 (d, J=17.4 Hz, 1H), 5.78 (d, J=10.9 Hz, 1H), 4.03 (s, 3H); LC/MS (ESI+) m/z 165 (M+H)+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 33332-25-1, its application will become more common.

Reference:
Patent; AbbVie S.a.r.l.; Galapagos NV; Altenbach, Robert J.; Bogdan, Andrew; Cowart, Marlon D.; Esmieu, William Ramesh; Gfesser, Gregory A.; Greszler, Stephen N.; Koenig, John R.; Kym, Philip R.; Liu, Bo; Malagu, Karine Fabienne; Patel, Sachin V.; Scanio, Marc J.; Searle, Xenia B.; Voight, Eric; Wang, Xeuqing; Yeung, Ming C.; (202 pag.)US2017/15675; (2017); A1;,
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. 1458-18-0, name is Methyl 3-amino-5,6-dichloropyrazine-2-carboxylate, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 1458-18-0

a) 3-Amino-6-bromo-5-(2-methoxy-ethylamino)-pyrazine-2-carboxylic acid methyl esterTo a mixture of 3-amino-5,6-dichloro-pyrazine-2-carboxylic acid methyl ester [CAS 1458-18-0] and 3-amino-6-bromo-5-chloro-pyrazine-2-carboxylic acid methyl ester [CAS 14340-25-1] (799 mg, 3 mmol) in DMF was added 2-methoxy-ethylamine (0.31 ml, 3.6 mmol) and NEt3 (2.09 ml, 15 mmol) and the mixture was stirred at r.t. for 3.5 h. The reaction mixture was poured into water (150 ml) and extracted with toluene (2×150 ml). The organic layers were washed with half-saturated aq. sodium chloride, combined, dried with Na2SO4 and evaporated. The residue was purified by chromatography on silica gel (cyclohexane/EtOAc 100:0 to 0:100%) to provide the title compound together with 3-amino-6-chloro-5-(2-methoxy-ethylamino)-pyrazine-2-carboxylic acid methyl ester (about 1:1) as colorless solid. This mixture was used for the next step.HPLC: RtH4=0.77 min; ESIMS [M+H]+=305.1; (Cl-pyrazine: HPLC: RtH4=0.73 min; ESIMS [M+H]+=261.1).

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 1458-18-0.

Reference:
Patent; BADIGER, Sangamesh; CHEBROLU, Murali; HURTH, Konstanze; JACQUIER, Sebastien; LUEOEND, Rainer Martin; MACHAUER, Rainer; RUEEGER, Heinrich; TINTELNOT-BLOMLEY, Marina; VEENSTRA, Siem Jacob; VOEGTLE, Markus; US2012/184539; (2012); A1;,
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. 1458-18-0, name is Methyl 3-amino-5,6-dichloropyrazine-2-carboxylate belongs to pyrazines compound, it is a common compound, a new synthetic route is introduced below. Safety of Methyl 3-amino-5,6-dichloropyrazine-2-carboxylate

To a solution of methyl 3-amino-5,6-dichloro-2-pyrazinecarboxylate (0.444 g, 2.0 mmol) in tetrahydrofuran (5 mL)/water (10 mL)/toluene (20 mL) was added phenyl boronic acid (0.536 g, 4.4 mmol), sodium carbonate (0.699 g, 6.6 mmol) and tetrakis(triphenylphosphine)-palladium(0) (0.116 g, 0.10 mmol). The reaction was evacuated and purged with nitrogen several times before being refluxed for 6 h. The organic layer was separated and the aqueous layer extracted with toluene (3 x 20 mL). The combined organic extracts were dried over magnesium sulfate, filtered and evaporated under reduced pressure to give methyl 3-amino-6-chloro-5-phenyl-2-pyrazinecarboxylate as a yellow solid (0.43 g, 82%).

The synthetic route of 1458-18-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Biotron Limited; Gage, Peter William; Ewart, Gary Dinneen; Wilson, Lauren Elizabeth; Best, Wayne; Premkumar, Anita; US2015/313909; (2015); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 14399-37-2, 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. 14399-37-2, name is 3,6-Dichloropyrazin-2-amine belongs to pyrazines compound, it is a common compound, a new synthetic route is introduced below.

To a 200 mL round bottom flask was added Na2S (10.816 g, 44wt% containing crystalline water, 60.978mmol) and toluene (100 mL). The mixture was heated to reflux, and water was removed with a Dean-Stark trap (about 5~6 mL water was distilled out). After cooling, the mixture was concentrated to dry.To above round bottom flask was added Y7d (5.000 g, 30.489mmol) and 2-methylbutan-2-ol (50 mL), the reaction was heated to reflux and stirred for 36 h. After cooling to 25 C, the mixture was filtered. The solvent of the filtrate was exchanged with n-heptane (5 V*3 times, based on Y7d), and finally concentrated to IV residue. THF (25 mL) was charged to the residue at 25 C and stirred. The suspension was filtered and washed with THF/n-heptane (5 mL/5 mL) to give a brown solid (6.200 g).To another 200 mL round bottom flask was added above brown solid (6.200 g),10% brine (25 mL), Me-THF (30 mL) and n-BmNBr (9.829 g, 30.489 mmol). The mixture was stirred for 0.5 h at room temperature, and the phases were separated. The organic phase was washed with 20% brine (25 mL), and exchanged the solvent with /.vo-propanol (5 V *3 times, based on Y7d) to give the /.vo-propanol solution of Y7c (27.000g, 99.2% purity by HPLC area, 58.08% assay yield). 1H NMR (400 MHz, DMSO-d6) d = 6.88 (s, 1H), 2.97 – 2.92 (m, 14H),1.38 – 1.31 (m, 14H), 1.13 – 1.04 (m, 14H), 0.73 – 0.69 (t, 21H). The advantage of the use of n- Bu4NBr (or other corresponding tert-alkylaminohalogenide) is easier workup and purification.

The synthetic route of 3,6-Dichloropyrazin-2-amine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NOVARTIS AG; FEI, Zhongbo; ZHANG, Hao; JIA, Huanqing; WANG, Hui; WANG, Jianhua; LI, Wei; LIN, Xiaohui; MIN, Zhongcheng; (91 pag.)WO2020/65452; (2020); 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. 5424-01-1, name is 3-Aminopyrazine-2-carboxylic acid, A new synthetic method of this compound is introduced below., Quality Control of 3-Aminopyrazine-2-carboxylic acid

15 g of 3-aminopyrazine-2-carboxylic acid was added to 200 ml of methanol.Add 10 ml of thionyl chloride, stir overnight at room temperature, and concentrate.200 ml of toluene was added and concentrated to give 18 g of 3-aminopyrazine-2-carboxylic acid methyl ester.

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; Changsha Shencheng Biological Technology Co., Ltd.; Bu Gonggaofamingren; (5 pag.)CN107513041; (2017); A;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 5521-58-4, 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. 5521-58-4, name is 5-Methylpyrazin-2-amine, This compound has unique chemical properties. The synthetic route is as follows.

Step 3: 4-[3-(5-Methyl-pyrazin-2-yl)-ureido]-3-(pyridin-3-ylmethoxy)-benzoic acid methyl ester. To a stirred, cooled (about 0 C.) solution of 4-amino-3-(pyridin-3-ylmethoxy)-benzoic acid methyl ester (258 mg, 1.0 mmol) in toluene (3.0 mL) was added triethylamine (139 muL, 1.0 mmol) and triphosgene (98 mg, 0.33 mmol). After stirring for 30 minutes, 5-methyl-2-amino pyrazine (109 mg, 1.0 mmol) was added and the reaction was heated to 65 degrees C. The reaction was allowed to cool to room temperature, then diluted with ethyl acetate (50 mL) and water (50 mL). A precipitate formed which was filtered and dried under reduced pressure to yield the desired material as a white solid (47% yield). 1H-NMR (400 MHz, d6-DMSO) delta10.29 (s, 1H), 8.79 (s, 1H), 8.68 (d, 1H, 8.59 (br s, 1H), 8.48 (d, 1H), 7.70 (s, 1H), 7.62 (d, 1H), 7.51 (m, 1H), 5.32 (s, 2H), 3.88 (s, 3H), 2.32 (s, 3H).

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

Reference:
Patent; Keegan, Kathleen S.; Kesicki, Edward A.; Gaudino, John Joseph; Cook, Adam Wade; Cowen, Scott Douglas; Burgess, Laurence Edward; US2003/69284; (2003); A1;,
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. 54608-52-5, name is 2-Hydrazinopyrazine, This compound has unique chemical properties. The synthetic route is as follows., Formula: C4H6N4

General procedure: To a stirred solution of2-hydrazinopyridines 1a-k or 2-hydrazinopyrazines 2a-f (1equiv.) and aldehyde 3a-k (1equiv.) in polyethyleneglycol (PEG) (10 mL) were added p-TsOH (5 mol%)) and DDQ (2 equiv.). The mixture was stirred at reflux untilthe starting material was completely consumed (monitored by TLC, 1h) and then cooled down to roomtemperature. After filtration and evaporation of solvent from the filtrate, the resulting residue was purified bysilica gel column chromatography (EtOAc/Hexane, 3:7 v/v), affording the pure N-fused 1,2,4-triazolederivative, [1,2,4]triazolo[4,3-a]pyridines 4a-k & [1,2,4]triazolo[4,3-a]pyrazines 5a-f.

According to the analysis of related databases, 54608-52-5, the application of this compound in the production field has become more and more popular.

Reference:
Article; Bhatt, Ashish; Singh, Rajesh K.; Kant, Ravi; Arkivoc; vol. 2018; 7; (2018); p. 236 – 247;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Some common heterocyclic compound, 6270-63-9, name is Pyrazin-2(1H)-one, molecular formula is C4H4N2O, 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. SDS of cas: 6270-63-9

1-(4-amino-3-fluoro-phenyl)-1H-pyrazin-2-one (prepared from 2-fluoro-4-iodoaniline by reaction with 1H-pyrazin-2-one, Cu(I)I, N,N’-dimethylethylenediamine and cesium carbonate in dioxane at 120 C.)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 6270-63-9, its application will become more common.

Reference:
Patent; Zbinden, Katrin Groebke; Haap, Wolfgang; Hilpert, Hans; Panday, Narendra; Ricklin, Fabienne; Wirz, Beat; US2006/247238; (2006); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 486424-37-7, 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. 486424-37-7, name is 3-Amino-6-bromopyrazine-2-carboxylic acid, This compound has unique chemical properties. The synthetic route is as follows.

3-amino-6-bromopyrazine-2-carboxylic acid (500 mg, 2.29 mmol), HOBT (464 mg, 3.44 mmol) and EDCI (660 mg, 3.44 mmol) were dissolved in dry DMF (20 mL), and the resulting solution was stirred for 6 hours. Then 3-fluoroaniline (305 mg, 2.75 mmol) and Et3N (0.43 mL) was added to the mixture. After being stirred overnight, the mixture was diluted with water and extracted with EtOAc. The combined organic phases were washed with brine, dried over Na2S04, filtered and evaporated. The crude product was purified by prep-TLC (PE : EtOAc = 6 : 1) to give the pure product of 3-amino-6-bromo-N-(3-fluorophenyl)pyrazine-2- carboxamide (500 mg, yield: 68%). XH-NMR (CDC13, 400 MHz) delta 9.44 (s, 1H), 8.22 (s, 1H), 7.59 (d, J= 11.2 Hz, 1H), 7.24-7.27 (m, 2H), 6.79-6.82 (m, 1H), 3.21 (s, 2H). MS (M+H)+: 311/ 313.

The chemical industry reduces the impact on the environment during synthesis 3-Amino-6-bromopyrazine-2-carboxylic acid. I believe this compound will play a more active role in future production and life.

Reference:
Patent; MERCK SHARP & DOHME CORP.; DAI, Xing; LIU, Hong; PALANI, Anandan; HE, Shuwen; NARGUND, Ravi; XIAO, Dong; ZORN, Nicolas; DANG, Qun; MCCOMAS, Casey, C.; PENG, Xuanjia; LI, Peng; SOLL, Richard; WO2014/209727; (2014); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem