Category: 17231-51-5

Some common heterocyclic compound, 17231-51-5, name is 3-Amino-6-bromopyrazine-2-carbonitrile, molecular formula is C5H3BrN4, 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: 3-Amino-6-bromopyrazine-2-carbonitrile

Step 2. 6-bromo-3-chloropyrazine-2-carbonitrileTo a solution of 3-amino-6-bromopyrazine-2-carbonitrile (587 mg, 2.95 mmol) in acetonitrile (29.4 mL) was added copper(II) chloride (470 mg, 3.5 mmol). The reaction was heated to 60 C. for 10 min, then t-butyl nitrite (510 muL, 4.3 mmol) was added drop-wise. The reaction was held at 60 C. for 16 h at which point LCMS indicated complete reaction. The reaction was cooled to ambient temperature and partitioned between 1N HCl and EtOAc and the phases were separated. The organic phase was washed 2× with water followed by brine, then dried over MgSO4 and concentrated in vacuo to provide the crude product which crystallized upon standing The product was purified (120 g prepacked SiO2 cartridge, 85 mL/min, gradient from 0-20% EtOAc/hexanes over 12 min) to recover the desired product, 442 mg. 1H NMR (300 MHz, CDCl3): delta 8.68 (s, 1H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 17231-51-5, its application will become more common.

Reference:
Patent; Rodgers, James D.; Shepard, Stacey; Arvanitis, Argyrios G.; Wang, Haisheng; Storace, Louis; Folmer, Beverly; Shao, Lixin; Zhu, Wenyu; Glenn, Joseph; US2010/298334; (2010); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

17231-51-5, name is 3-Amino-6-bromopyrazine-2-carbonitrile, 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. Safety of 3-Amino-6-bromopyrazine-2-carbonitrile

Step A Synthesis of 2-amino-3-cyano-5-(trimethylsilylethynyl)pyrazine as an intermediate A solution of 3.0 grams (0.015 mole) of 2-amino-3-cyano-5-bromopyrazine and 2.1 grams (0.021 mole) of trimethylsilylacetylene in 50 mL of acetonitrile is stirred, and 10.6 mL of triethylamine, 0.13 gram of copper iodide, and 0.29 gram of bis(triphenylphosphine)palladium(II) chloride are added in order. Upon completion of addition, the reaction mixture is stirred at ambient temperature for about 20 hours. The reaction mixture is warmed to 70 C., where it is stirred for about 7.5 hours. After this time, the reaction mixture is concentrated under reduced pressure to a residue. The residue is dissolved in ethyl acetate, and the solution is washed with 50 mL of aqueous, dilute hydrochloric acid. The organic layer is dried with magnesium sulfate and filtered. The filtrate is concentrated under reduced pressure to a residue. The residue is subjected to column chromatography on silica gel. Elution is accomplished using tetrahydrofuran/methylene chloride combinations. The product-containing fractions are combined and concentrated under reduced pressure, yielding 2-amino-3-cyano-5-(trimethylsilylethynyl)pyrazine.

The synthetic route of 17231-51-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; FMC Corporation; US5521190; (1996); A;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 17231-51-5, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 17231-51-5 name is 3-Amino-6-bromopyrazine-2-carbonitrile, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

Intermediate H (0192) 3-Amino-6-(4-chloro-2-fluorophenyl)pyrazine-2-carbonitrile (0193) To a solution of 3-amino-6-bromopyrazine-2-carbonitrile (2.00 g, 9.55 mmol) in 1,4-dioxane (48 mL), were added (4-chloro-2-fluorophenyl)boronic acid (1.66 g, 9.55 mmol) and aqueous Na2CO3 (2 M, 24 mL, 48 mmol) and the reaction mixture sparged with N2 gas for 10 min. Pd(dppf)Cl2.CH2Cl2 (0.349 g, 0.477 mmol) was then added and the reaction mixture sparged for an additional 10 min with N2 gas. The reaction vessel was sealed and heated for 3 hours at 80 Celsius. The mixture was cooled to rt, filtered through celite, and the filter cake washed with EtOAc (300 mL). The filtrate was washed with a 1:1 mixture of brine/H2O (2×100 mL). The organic phase was concentrated to dryness and subjected to FCC to give the title compound (1.99 g, 84%). MS (ESI): mass calcd. for C11H6ClFN4, 248.03; m/z found 249.0 [M+H]+. 1H NMR (400 MHz, CDCl3) delta 8.67 (d, J=2.0, 1H), 7.83 (m, 1H), 7.25-7.08 (m, 2H), 5.36 (s, 2H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-Amino-6-bromopyrazine-2-carbonitrile, and friends who are interested can also refer to it.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; Bacani, Genesis M.; Eccles, Wendy; Fitzgerald, Anne E.; Goldberg, Steven D.; Hack, Michael D.; Hawryluk, Natalie A.; Jones, William M.; Keith, John M.; Krawczuk, Paul; Lebsack, Alec D.; Lee-Dutra, Alice; Liu, Jing; McClure, Kelly J.; Meduna, Steven P.; Pippel, Daniel J.; Rosen, Mark D.; Sales, Zachary S.; US2015/259357; (2015); 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. 17231-51-5, name is 3-Amino-6-bromopyrazine-2-carbonitrile, This compound has unique chemical properties. The synthetic route is as follows., Application In Synthesis of 3-Amino-6-bromopyrazine-2-carbonitrile

Step 2: synthesis of 3,6-dibromopyrazine-2-carbonitrile (15) To a solution of copper(ii) bromide (1.432 g, 6.41 mmol) and tert-butylnitrite (0.769 mL, 6.41 mmol) in acetonitrile (40 mL) was added 3-amino-6-bromopyrazine-2-carbonitrile 14 (1.16 g, 5.83 mmol) in portions (in 2 h). The reaction was stirred for 2 h at 50 C. Quenched with 2N HCl solution and the resulting precipitate was collected. Purification by chromatography (CH2Cl2) gave pure 3,6-dibromopyrazine-2-carbonitrile 15 (820 mg, 53.5%). 1H-NMR (400 MHz, CDCl3) 8.66 (s, 1H). (m/z)=261, 263 and 265 (M+H)+.

According to the analysis of related databases, 17231-51-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Folmer, Brigitte Johanna Bernita; Man, de Adrianus Petrus Antonius; Gernette, Elisabeth Sophia; Corte Real Goncalves Azevedo, Rita; Ibrahim, Hemen; US2013/79341; (2013); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 17231-51-5, 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. 17231-51-5, name is 3-Amino-6-bromopyrazine-2-carbonitrile, This compound has unique chemical properties. The synthetic route is as follows.

Step 1: 3-Amino-6-bromo-N?-hydroxypyrazine-2-carboximidam ide To a 20m1 flask was added 3-amino-6-bromopyrazine-2-carbonitrile (600 mg, 3.01 mmol) inMeOH (12 ml) and cooled to 000. To the reaction mixture was added hydroxylaminehydrochloride (210 mg, 3.01 mmol) and triethylamine (0.420 ml, 3.01 mmol) and the mixturewas allowed to warm to room temperature as a precipitate formed. The precipitate was filtered off and washed with MeOH. The filtrate was concentrated under reduced pressure and the resulting solid triturated in MeOH to give a second crop of product. The solid was triturated in MeOH again and sonicated for l5mins until a suspension formed. The solid wasfiltered off and dried in a vacuum oven at 40C for 3 hours to afford the title compound;1H NMR (400MHz, DMSO-d6), O 10.38 (1H, 5), 8.15 (1H, 5), 7.64 (2H, brs), 5.88 (2H, 5).

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

Reference:
Patent; NOVARTIS AG; BELLENIE, Benjamin Richard; BLOOMFIELD, Graham Charles; BRUCE, Ian; CULSHAW, Andrew James; HALL, Edward Charles; HOLLINGWORTH, Gregory; NEEF, James; SPENDIFF, Matthew; WATSON, Simon James; (395 pag.)WO2015/162459; (2015); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 17231-51-5, name is 3-Amino-6-bromopyrazine-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 17231-51-5, category: Pyrazines

Step 2: synthesis of 3,6-dibromopyrazine-2-carbonitrile (15)To a solution of copper(ii) bromide (1.432 g, 6.41 mmol) and tert-butylnitrite (0.769 mL, 6.41 mmol) in acetonitrile (40 mL) was added 3-amino-6-bromopyrazine-2- carbonitrile 14 (1.16 g, 5.83 mmol) in portions (in 2h). The reaction was stirred for 2h at 50C. Quenched with 2N HC1 solution and the resulting precipitate was collected. Purification by chromatography (CH2CI2) gave pure 3,6-dibromopyrazine-2- carbonitrile 15 (820 mg, 53.5 %). 1H-NMR (400 MHz, CDC13) 8.66 (s, 1H). (m/z) = 261, 263 and 265 (M+H)+.

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; N.V. ORGANON; FOLMER, Brigitte, Johanna, Bernita; MAN, de, Adrianus, Petrus, Antonius; GERNETTE, Elisabeth, Sophia; CORTE REAL GONCALVES AZEVEDO, Rita; IBRAHIM, Hemen; WO2011/147764; (2011); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Related Products of 17231-51-5, The chemical industry reduces the impact on the environment during synthesis 17231-51-5, name is 3-Amino-6-bromopyrazine-2-carbonitrile, I believe this compound will play a more active role in future production and life.

Step A Synthesis of 2-amino-3-cyano-5-[3,5-di(trifluoromethyl)phenyl]pyrazine as an intermediate A stirred solution of 1.6 grams (0.008 mole) of 2-amino-3-cyano-5-bromopyrazine [prepared by the method of Taylor and Ray–JOC, 52, 3997 (1987)], 3.2 grams (0.012 mole) of 3,5-di(trifluoromethyl)phenylboronic acid commercially available or prepared by the method of Thompson and Gaudino–JOC, 49, 5237 (1984)], 4.3 grams (0.031 mole) of potassium carbonate and 0.3 gram of tetrakis(triphenylphosphine)palladium(0) in 150 mL of toluene is heated at 90 C. for about 20 hours. After this time, the reaction mixture is stirred with 100 mL of water, and the organic layer is separated. The organic layer is concentrated under reduced pressure to a residue. The residue is subjected to column chromatography on silica gel. The product-containing fractions are combined and concentrated under reduced pressure, yielding 2-amino-3-cyano-5-[3,5-di(trifluoromethyl)phenyl]pyrazine.

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, 3-Amino-6-bromopyrazine-2-carbonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; FMC Corporation; US5521190; (1996); A;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

17231-51-5, name is 3-Amino-6-bromopyrazine-2-carbonitrile, 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: 3-Amino-6-bromopyrazine-2-carbonitrile

Step A Synthesis of 2-amino-3-cyano-5-(trimethylsilylethynyl)pyrazine as an intermediate A solution of 3.0 grams (0.015 mole) of 2-amino-3-cyano-5-bromopyrazine and 2.1 grams (0.021 mole) of trimethylsilylacetylene in 50 mL of acetonitrile is stirred, and 10.6 mL of triethylamine, 0.13 gram of copper iodide, and 0.29 gram of bis(triphenylphosphine)palladium(II) chloride are added in order. Upon completion of addition, the reaction mixture is stirred at ambient temperature for about 20 hours. The reaction mixture is warmed to 70 C., where it is stirred for about 7.5 hours. After this time, the reaction mixture is concentrated under reduced pressure to a residue. The residue is dissolved in ethyl acetate, and the solution is washed with 50 mL of aqueous, dilute hydrochloric acid. The organic layer is dried with magnesium sulfate and filtered. The filtrate is concentrated under reduced pressure to a residue. The residue is subjected to column chromatography on silica gel. Elution is accomplished using tetrahydrofuran/methylene chloride combinations. The product-containing fractions are combined and concentrated under reduced pressure, yielding 2-amino-3-cyano-5-(trimethylsilylethynyl)pyrazine.

The synthetic route of 17231-51-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; FMC Corporation; US5521190; (1996); A;,
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. 17231-51-5, name is 3-Amino-6-bromopyrazine-2-carbonitrile, A new synthetic method of this compound is introduced below., SDS of cas: 17231-51-5

REFERENTIAL EXAMPLE II-9 In 10 mL of tetrahydrofuran was dissolved 0.50 g of 3-amino-6-bromo-2-pyrazinecarbonitrile. After adding 0.15 g of 60% sodium hydride, the mixture was stirred at room temperature for 15 minutes. Then, 0.7 mL of di-t-butyl dicarbonate and 0.10 g of 60% sodium hydride were successively added, and the mixture thus formed was stirred at room temperature for one hour. The reaction mixture was added to a liquid mixture consisting of 30 mL of ethyl acetate and 60 mL of water, pH was adjusted to 5 with 2 mol/L hydrochloric acid, and the organic layer was separated. The organic layer was washed successively with water and saturated aqueous solution of sodium chloride and dried on anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The residue thus obtained was purified by silica gel column chromatography [eluent: n-hexane:ethyl acetate=5:1] to obtain 0.30 g of t-butyl 5-bromo-3-cyano-2-pyrazinylcarbamate as a white-colored solid product. IR(KBr) cm-1: 2239, 1708 1H-NMR (CDCl3+DMSO-d6) delta: 1.57(9H,s), 7.41(1H,brs), 8.62(1 H,s)

The synthetic route of 17231-51-5 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 17231-51-5, 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 17231-51-5 as follows.

Step 1 [0188] A 50 mL RBF equipped with magnetic stir bar was charged with 1.0 g (1.0 eq.) Bromo amine, 1 .6 g (2.2 eq.) methyl Iodide, and 3.7 g (2.2 eq.) CsC03 in 25 ml DMF. The reaction was stirred at RT. The reaction mixture got dark and was let to stir overnight. LC/MS looks like previous runs. The reaction was partionned between EA and aq. Citric. The organics were washed with satd. bicarb, brine, dried and concentrated in vacuo to crude. Purification was done by Flash Chromatography (20 – 50 % EA-H). The fractions containing visible yellow product (even if some had some long wave impurities) were combined and concentrated then vacuum dried to afford 940 mgs of crystalline solid.

According to the analysis of related databases, 17231-51-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MALLINCKRODT LLC; FRESKOS, John, N.; WO2013/39851; (2013); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem