Pyrazines

Reference of 41270-66-0, A common heterocyclic compound, 41270-66-0, name is 5-Chloro-2,3-diphenylpyrazine, molecular formula is C16H11ClN2, 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.

30 g of 2-chloro-5,6-diphenylpyrazin and 131.22 g (0.3 mol) of 4-isopropylamino-1-butanol were added into a 500 mL flask, the mixture was heated to 190 C. and reacted at this temperature for 10 hours, cooled, samples were taken for testing, HPLC purity of the product was 63.5%. The reaction solution was poured into 1 L of ice water, the mixture was extracted with ether 200 mL¡Á3, the organic phases were combined and the solvent was concentrated to dryness, then the residue was purified by column chromatography, and 22.96 g of 4-[N-(5,6-diphenylpyrazin-2-yl)-N-isopropylamino]-1-butanol was obtained, HPLC purity was 97.2%, the molar yield was 56%. (0083) 1H-NMR data: 1H-NMR (400 MHz, CDCl3) delta 8.02 (s, 1H), 7.46 (d, 2H, J=7.6 Hz), 7.36 (d, 2H, J=7.2 Hz), 7.28-7.22 (m, 6H), 4.80-4.78 (m, 1H), 3.71 (t, 2H, J=6.4 Hz), 3.45 (t, 2H, J=7.6 Hz), 1.77-1.74 (m, 2H), 1.66-1.64 (m, 2H), 1.29 (d, 6H, J=6.8 Hz).

The synthetic route of 41270-66-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Seasons Biotechnology (Taizhou) Co., Ltd.; TANG, Fanghui; MA, Chi; JIA, Qiang; (11 pag.)US2018/29998; (2018); 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. 622392-04-5, name is 2-Bromo-5-iodopyrazine, A new synthetic method of this compound is introduced below., Recommanded Product: 2-Bromo-5-iodopyrazine

Step 1: N-1-(5-Iodo-pyrazin-2-yl)-2-methyl-propane-1,2-diamine To a solution of 2-bromo-5-iodopyrazine (CAS 622392-04-5) (250 mg, 878 mmol) in 0.7 ml of pyridine, was added 2-methylpropane-1,2-diamine (116 mg, 138 mul, 1.32 mmol, 1.5 equiv.) at room temperature. The colorless solution was stirred for 16 hours at 100 C. The reaction mixture was cooled and concentrated in vacuo. The crude material was used directly in the next step.

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; Green, Luke; Guba, Wolfgang; Jaeschke, Georg; Jolidon, Synese; Lindemann, Lothar; Ricci, Antonio; Rueher, Daniel; Stadler, Heinz; Vieira, Eric; US2011/251169; (2011); A1;,
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Pyrazine | C4H4N2 – PubChem

33332-25-1, name is Methyl 5-chloropyrazine-2-carboxylate, 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. Recommanded Product: 33332-25-1

A mixture of 4-aminotetrahydropyran (500 mg, 4.94 mmol) and methyl 2-chloropyrazine-5-carboxylate (770 mg, 4.46 mmol) in DMF (5 mL) containing N,N-diisopropylethylamine (1.0 mL, 5.7 mmol) was stirred at 55 C. for 17 hrs. The reaction mixture was concentrated and the residue was partitioned between ether (25 mL) and hydrochloric acid (1N, 25 mL). The aqueous layer was further extracted with ether (25 mL). The resulting aqueous layer was first treated with sodium chloride (10 g) and then extracted with methylene chloride (3¡Á50 mL). The organic layer was washed with brine and dried over sodium sulfate. Solvents were evaporated to give an oil which slowly crystallized as methyl 2-(N-tetrahydropyran-4-yl)-aminopyrazine-5-carboxylate (900 mg, 85%). MS calcd for C11H15N3O3 (m/e) 237, obsd 238.1 (M+H).

The synthetic route of 33332-25-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Bolin, David Robert; Cheung, Adrian Wai-Hing; Firooznia, Fariborz; Hamilton, Matthew Michael; Li, Shiming; McDermott, Lee Apostle; Qian, Yimin; Yun, Weiya; US2007/123504; (2007); A1;,
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Pyrazine | C4H4N2 – PubChem

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 5521-58-4 as follows. Recommanded Product: 5-Methylpyrazin-2-amine

Oxalyl chloride (1.9 mL, 22.2 mmol) and DMF (1 drop) were added to a solution of 3- [(phenylmethyl)oxy]-5-[(3^-tetrahydrofuran-3-yloxy]benzoic acid (5.8 g, 18.5 mmol) in DCM (100 mL) and the mixture stirred at RT for 16 hours. The mixture was evaporated in vacuo to a residue which was redissolved in DCM (25 mL) and added to a stirred mixture of 2-amino-5-methylpyrazine (2.22 g, 20.35 mmol) and pyridine (1.81 mL, 22.2 mmol) in DCM (100 mL) at 50C – 1O0C. The mixture was stirred at RT for 18 hours, the DCM evaporated in vacuo to give a residue which was partitioned between water (50 mL) and ethyl acetate (125 mL). The organic layer was washed with brine, dried (MgSO4) and evaporated to a residue which was chromatographed on silica, eluting with 60% ethyl acetate in isohexane, to give the desired material (5.1 g). 1H NMR delta (CDCl3): 2.1 – 2.2 (m, 2H), 2.5 (s, 3H), 3.8 – 3.95 (m, 4H), 4.9 (m, IH), 5.0 (s, 2H), 6.6 (s, IH), 6.95 (s, IH), 7.05 (s, IH), 7.35 (m, 5H), 8.05 (s, IH), 8.3 (s, IH), 9.5 (s, IH); m/z 406 (M+H)+.

According to the analysis of related databases, 5521-58-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2006/125972; (2006); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

These common heterocyclic compound, 14508-49-7, name is 2-Chloropyrazine, 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. Computed Properties of C4H3ClN2

In a sealed tube, 2-chloropyrazine (1.0 g, 8.7 mmol, 1 equiv) was heated withethanolic methylamine (33% w/w; 4.0 g, 43.6 mmol, 5 equiv) at 95 C for 1 h.Solvent and excess of methylamine were then removed under reduced pressure. Theresidue was then dissolved in dichloromethane and washed three times with water.The organic phase was then evaporated under reduced pressure and the crude productwas further purified by flash chromatography on silica gel (EtOAc/Et2O= 1:6 to 1:4).The product S2 was obtained as a colorless oil (0.73 g, 6.7 mmol, 77% yield), whichsolidified as a light brown solid. The spectra are in agreement with the literaturereport.1

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

Reference:
Article; Huang, Qi; Qin, Ling; Zard, Samir Z.; Tetrahedron; vol. 74; 40; (2018); p. 5804 – 5817;,
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. 19847-12-2, name is Pyrazinecarbonitrile, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of Pyrazinecarbonitrile

To a solution of pyrazine-2-carbonitrile (1.0 g, 9.52 mmol) in methanol (20 mL) was addedNaOCH3 (0.10 g, 1.90 mmol). The resulting mixture was heated with stirring at rt for 12 hrs. Tothe reaction mixture was added NH4C1 (0.51 g, 9.52 mmol). After being heated under reflux for 3 hrs, the resulting reaction mixture was concentrated in vacuo. The residue was suspended in ethanol (30 mL). The suspension was heated under reflux for 1 hr, then cooled to rt and filtered. The filtrate was concentrated in vacuo to give pyrazine-2-carboxamidine hydrochloride (1.2 g),which was used in the next step without further purification.

According to the analysis of related databases, 19847-12-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; CHENG, Zhanling; WANG, Min; YANG, Song; (208 pag.)WO2016/107832; (2016); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 136927-64-5,Some common heterocyclic compound, 136927-64-5, name is 1-Chloropyrrolo[1,2-a]pyrazine, molecular formula is C7H5ClN2, 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.

Compound C21 (500 mg, 2.22 mmol), 1-chloropyrrolo[1,2-a]pyrazine (339 mg, 2.22 mmol), cesium carbonate (796 mg, 2.44 mmol), and palladium(ll) acetate (53 mg,0.22 mmol) were combined in 1,4-dioxane (15 mL), and the solution was degassed with nitrogen for 15 minutes. Di-tert-butyl[3,4, 5,6-tetramethyl-2?, 4?,6?-tri(propan-2-yl) bi phenyl2-yl]phosphane (214 mg, 0.444 mmol) was added to the reaction mixture, which wasthen degassed for an additional 2 minutes. The reaction mixture was heated to 100 00 in a microwave reactor for 6 hours, whereupon it was cooled to room temperature andfiltered through diatomaceous earth. The filter cake was washed with ethyl acetate, andthe combined filtrates were concentrated in vacuo. Silica gel chromatography (Gradient:20% to 80% ethyl acetate in heptane) was followed by three triturations with heptane;the resulting material was purified again using silica gel chromatography (Gradient:50% to 70% ethyl acetate in heptane) to provide the product as a pale yellow solid.Yield: 361 mg, 1.06 mmol, 48%. LCMS m/z 342.1 [M+H]. 1H NMR (400 MHz, ODd3) oe9.05 (5, 1H), 7.82 (d, J=2.5 Hz, 1H), 7.70 (d, J=2.3 Hz, 1H), 7.68-7.66 (m, 1H), 7.50(dd, J=2.5, 1.4 Hz, 1H), 7.37 (d, J=8.2 Hz, 1H), 7.09 (d, J=4.9 Hz, 1H), 7.01-6.98 (m,1H), 6.89 (dd, J=2.5, 4.1 Hz, 1H), 2.36 (5, 6H).

The synthetic route of 136927-64-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PFIZER INC.; GRAY, David Lawrence Firman; DAVOREN, Jennifer Elizabeth; DOUNAY, Amy Beth; EFREMOV, Ivan Viktorovich; MENTE, Scot Richard; SUBRAMANYAM, Chakrapani; WO2015/166370; (2015); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 939412-86-9, name is (3-Chloropyrazin-2-yl)methanamine hydrochloride, 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 939412-86-9, name: (3-Chloropyrazin-2-yl)methanamine hydrochloride

(g) N-((3-chloropyrazin-2-yl)methyl)-1-oxooctahydropyrido[1,2-c][1,3]oxazine-7-carboxamide To a solution of 1-oxooctahydropyrido[1,2-c][1,3]oxazine-7-carboxylic acid (3.13 g, 15.7 mmol) in THF (100 mL) was added (3-chloropyrazin-2-yl)methanamine hydrochloride (2.8 g, 15.7 mmol), TEA (4.8 g, 47.2 mmol) and HATU (6 g, 15.7 mmol). The mixture was stirred at room temperature for 2 h. The reaction was complete detected by LCMS. The reaction mixture was treated with DCM and water, the organic layer was dried and concentrated. The residue was purified by column chromatography on silica gel eluted with DCM/THF=5/1 to give N-((3-chloropyrazin-2-yl)methyl)-1-oxooctahydropyrido[1,2-c][1,3]oxazine-7-carboxamide (4.7 g, 92%). 1H-NMR (CDCl3, 400 MHz) delta 1.40-1.49 (m, 1H), 1.71-1.92 (m, 3H), 2.04-2.26 (m, 2H), 2.43-2.57 (m, 1H), 2.81-2.97 (m, 1H), 3.31-3.42 (m, 1H), 4.13-4.27 (m, 2H), 4.46-4.56 (m, 1H), 4.64 (d, J=4.70 Hz, 2H), 8.29 (d, J=2.35 Hz, 1H), 8.44 (d, J=2.35 Hz, 1H).

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; KIM, RONALD M.; Liu, Jian; Gao, Xiaolei; Boga, Sobhana Babu; Guiadeen, Deodialsingh; Kozlowski, Joseph A.; Yu, Wensheng; Anand, Rajan; Yu, Younong; Selyutin, Oleg B.; Gao, Ying-Duo; Wu, Hao; Liu, Shilan; Yang, Chundao; Wang, Hongjian; US2014/206681; (2014); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Related Products of 61655-72-9,Some common heterocyclic compound, 61655-72-9, name is 6-Chloro-N,N-dimethylpyrazin-2-amine, molecular formula is C6H8ClN3, 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 mixture of 6- cMoro-N,N-dimethylpyrazin-2-amine (11-2) ( 1 g, 6.3 mmol) and pyridin-4-yl boronic acid (1.06 g, 8.6 mmol, 1.35 eq) were suspended in dimethoxyethane and water (10:1 ) in a heavy wall pressure vessel. The reaction mixture was purged with argon for 10 min. Sodium carbonate (2.0 g, 1 ,6 mmol, 3 eq) and tetrakis(triphenylphosphine) palladium (0.650 g, 0.57 mmol) were added and the reaction mixture was heated at 1 10 ¡ãC for 15 hrs. The reaction mixture was cooled to ambient temperature and filtered though a medium frit sintered glass funnel filled with Celite. The filtrate was concentrated under reduced pressure, dissolved in dichloromethane and washed with water (3 x 5 mL). The organic layer was dried with sodium sulfate and concentrated under reduced pressure. The product 11-3 was purified over silica gel column using ethylacetate and hexane (2:3 v/v) eluent. The title compound 11-3 was obtained as yellow solid (1 , 1 g) in 75percent (gravimetric) yield. HPLC (tr/purity): 10.7 min, > 90percent (HPLC method A); ESI m/z (MeOH) : 201.10 (MH ).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 6-Chloro-N,N-dimethylpyrazin-2-amine, its application will become more common.

Reference:
Patent; THE TRUSTEES OF COLUMBIA UNIVERSITY IN THE CITY OF NEW YORK; ARANCIO, Ottavio; WATTERSON, Daniel, Martin; PELLETIER, Jeffrey, Claude; ROY, Saktimayee, Mitra; WO2014/145485; (2014); A2;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 59303-10-5, name is 2-Chloro-5-methylpyrazine, 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 59303-10-5, Recommanded Product: 59303-10-5

PREPARATION EXAMPLE 2: N-rri -(5-methoxypyrazin-2-vncvclopropyllmethyll-2- (trifluoromethyl)benzamide (compound A.26)Step 1 : 2-(bromomethyl)-5-chloro-pyrazine5.0 g of 2-chloro-5-methyl-pyrazine, 6.9 g of N-bromosuccinimide and 0.33 g of 2,2′- azobis(2-methylpropionitrile) were suspended in 67 ml of chlorobenzene. The yellow mixture was heated to 130C and stirred for 4 hours. Then the mixture was cooled to ambient temperature, diluted with ethyl acetate and an aqueous solution of sodium thiosulfate was added. After extraction the phases were separated, the organic layer was washed with brine, dried over anhydrous sodium sulphate and evaporated. The residue was purified by flash chromatography on silica gel with cyclohexane/ethyl acetate (2:1 ) as eluent. Thus, 5.52 g of 2-(bromomethyl)-5-chloro-pyrazine was obtained as a brown oil. 1H-NMR (CDCI3): 8.57 ppm (s, 1 H), 8.49 ppm (s, 1 H), 4.54 ppm (s, 2H).

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; SYNGENTA PARTICIPATIONS AG; LOISELEUR, Olivier; PITTERNA, Thomas; O’SULLIVAN, Anthony, Cornelius; LUKSCH, Torsten; WO2013/64518; (2013); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem