Category: 113305-94-5

Reference of 113305-94-5, A common heterocyclic compound, 113305-94-5, name is 5-Aminopyrazine-2-carbonitrile, molecular formula is C5H4N4, 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.

Synthesis 23-1 -B 5-(1 H-Pyrrolo[2,3-c]pyridin-5-ylamino)pyrazine-2-carbonitrile (CC-001 ) A mixture of tert-butyl 5-chloro-1 H-pyrrolo[2,3-c]pyridine-1-carboxylate (0.030 g, 0.119 mmol), 5-aminopyrazine-2-carbonitrile (0.017 g, 0.142 mmol), cesium carbonate (0.077 g, 0.237 mmol), Xantphos (0.011 g, 0.019 mmol) and tris(benzylideneacetone)dipalladium (0) (0.009 g, 0.010 mmol) in dioxane (0.8 mL) was degassed by bubbling argon through the mixture for 10 minutes. The sealed reaction vessel was heated to 150C for 1 hour in a microwave reactor. The crude mixture was filtered through an SCX-2 acidic resin cartridge, eluting with 2 M ammonia in methanol. The basic filtrate was concentrated and purified by column chromatography to give the title compound (0.018 g, 0.054 mmol, 45%). LC-MS (3) Rt = 1.30 min; m/z (ESI+) 237 (M+H).

The synthetic route of 113305-94-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CANCER RESEARCH TECHNOLOGY LIMITED; WO2009/103966; (2009); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 113305-94-5,Some common heterocyclic compound, 113305-94-5, name is 5-Aminopyrazine-2-carbonitrile, molecular formula is C5H4N4, 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 5-aminopyrazine-2-carbonitrile (44.3 mg, 0.37 mmol) in THF (10 mL) was added NaH (24.4 mg, 0.61 mmol) at 0 C. The resulting mixture was stirred at ambient temperature for 1 h. A solution of compound 3 05-5 (120 mg, 0.3 lmmol) in THF (2 mL) was added and stirred at 55 C for 3.5 h. The reaction mixture was quenched with ice water and extracted with ethyl acetate. The organic layer was washed with water and brine, dried over anhydrous Na2SO4 and concentrated. The crude product was purified by column chromatography (hexanes/ethyl acetate: 3/1) to afford the title compound 306-5 as a yellow solid (110 mg, 77 % yield).

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

Reference:
Patent; PHARMAENGINE, INC.; CAI, Xiong; QIAN, Changgeng; WANG, Yanong Daniel; (98 pag.)WO2017/132928; (2017); A1;,
Pyrazine – Wikipedia,
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 113305-94-5 as follows. category: Pyrazines

2-Amino-5-cyano pyrazine (0.25 g, 2.08 mmol) was dissolved in a mixture of 3:1 THF and DCM (40 mL) and pyridine (0.49 g, 6.2 mmol) was added. The mixture was stirred for 15 minutes then phenylchloroformate (0.97 g, 6.2 mmol) was added and the reaction mixture was heated at 50 C. for 2 hours. The reaction mixture was allowed to cool to room temperature then DCM (40 mL) and water (25 mL) were added. The separated organic layer was washed with water (2*25 mL), brine (25 mL), dried (Na2SO4) and the solvents removed under reduced pressure to give the title compound (0.8 g) which was used without further purification.

According to the analysis of related databases, 113305-94-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Boyle, Robert George; Boyce, Richard Justin; US2014/323484; (2014); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 113305-94-5,Some common heterocyclic compound, 113305-94-5, name is 5-Aminopyrazine-2-carbonitrile, molecular formula is C5H4N4, 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.

ii) 5-Aminopyrazine-2-carbonitrile (0.208 mmol) in acetonitrile (1 mL) was added portionwise to a stirred solution of copper (II) bromide (0.25 mmol) and t-butylnitrite (0.31 mmol) in acetonitrile (2 mL) and the reaction mixture was maintained at 60 C. for 1 h. The reaction was diluted with ethyl acetate (15 mL) and washed twice with 1N HCl (aqueous). Purification was done by chromatography (silica, hexane; ethyl acetate) to yield the title compound (49%). 1H NMR (CDCl3) delta (ppm): 8.83 (s, 1H); 8.71 (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 5-Aminopyrazine-2-carbonitrile, its application will become more common.

Reference:
Patent; AstraZeneca AB; NPS PHARMACEUTICALS, INC.; US2007/37820; (2007); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 113305-94-5, 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. 113305-94-5, name is 5-Aminopyrazine-2-carbonitrile belongs to pyrazines compound, it is a common compound, a new synthetic route is introduced below.

EXAMPLE 26 (E)-5-((4-Amino-8-(4-(2-cyanovinyl)-2,6-dimethylphenyI)-6-fluoroquinazoIin-2- yl)amino)pyrazine-2-carbonitrile- Compound 26 Synthesis of (E)-5-((4-amino-8-(4-(2-cyanovinyl)-2,6-dimethylphenyl)-6- fluoroquinazoIin-2-yl)amino)pyrazine-2-carbonitrile (compound 26) Compound 26 [0314] Compound 20d (92 mg, 0.21 mmol), 5-aminopyrazine-2-carbonitrile (60 mg, 0.50 mmol, Ark Pharm Inc, AK-21935), N,N-diisopropylethylamine (174 1 .0 mmol), (9,9- dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (24 mg, 0.042 mmol) and palladium (II) acetate (9 mg, 0.042 mmol) were combined under argon in N-methyl-2-pyrrolidone (2 mL). The reaction was heated at 100C in a sealed vessel for 7 hours. The reaction mixture was cooled down to room temperature, purified by silica gel chromatography (gradient from 50- 100% ethyl acetate in wo-hexanes) and then re-purified by reverse phase chromatography (5- 100% acetonitrile in water with 0.1 % trifluoroacetic acid) to afford the TFA salt of compound 26. ‘H NMR (400 MHz, DMSO-flfc) delta 9.10 (s, 1 H), 8.20 (s, 1 H), 7.74 (d, J = 16.7 Hz, 1 H), 7.77 – 7.60 (m, 2H), 7.57 (s, 2H), 6.56 (d, J = 16.7 Hz, 1 H), 1.94 (s, 6H). LCMS (m/z) 436.9 [M+H], Tr = 3.59 min (LCMS method 1 ).

The synthetic route of 5-Aminopyrazine-2-carbonitrile has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GILEAD SCIENCES, INC.; INSTITUTE OF ORGANIC CHEMISTRY AND BIOCHEMISTRY OF THE AS CR, V.V.I.; JANSA, Petr; SIMON, Tetr; LANSDON, Eric; HU, Yunfeng, Eric; BASZCZYNSKI, Ondrejj; DEJMEK, Milan; MACKMAN, Richard, L.; (185 pag.)WO2016/105564; (2016); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 113305-94-5,Some common heterocyclic compound, 113305-94-5, name is 5-Aminopyrazine-2-carbonitrile, molecular formula is C5H4N4, 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-Aminopyrazine-2-carbonitrile (5.45 mg, 0.045 mmol), Xantphos (1.749 mg, 3.02 mumol), tris(dibenzyiideneacetone)dipalladium(0) (1.384 mg, 1.511 mumol), and cesium carbonate (24.62 mg, 0.076 mmol) were added to tert-butyl 4-((2-chloro-5-(4-methoxyphenyl)pyridin- 4-ylamino)methyl)-4-fluoropiperidine-1-carboxylate (17 mg, 0.038 mmol) in a 0.2 mL microwave reaction vial. The vial was sealed and an inert atmosphere was introduced before dry dioxane (291 muL) was added. Nitrogen was bubbled through the mixture for 5 min. The mixture was heated at 150 0C for 1 hr by microwave irradiation. After cooling the mixture was diluted with 20% dichloromethane in MeOH and loaed onto a preparative thin layer chromatography plate. Elution with 50% EtOAc in hexane gave tert-butyl 4-((2-(5- cyanopyrazin-2-ylamino)-5-(4-methoxyphenyl)pyridin-4-ylamino)methyl)-4- fluoropiperidine-1-carboxylate (1.5 mg, 2.81 mumol, 7% yield) as a light yellow powder. LCMS (4) Rt = 2.35 min; m/z (ESI+) 534 (MH+). Trifluoroacetic acid (0.1 mL, 1.298 mmol) was added to tert-butyl 4-((2-(5-cyanopyrazin-2-ylamino)-5-(4-methoxyphenyl)pyridin-4- ylamino)methyl)-4-fluoropiperidine-1-carboxylate (1.5 mg, 2.81 mumol) dissolved in dichloromethane (0.5 mL) and the solution was stirred for 1 hr. The volatiles were removed in vacuo and the crude product was purified by ion exchange on lsolute SCX Il acidic resin (1 g), followed by preparative thin layer chromatography, eluting with 10% MeOH / 1% NH3 / 89% dichloromethane, to give 5-(4-((4-fluoropiperidin-4- yl)methylamino)-5-(4-methoxyphenyl)pyridin-2-ylamino)pyrazine-2-carbonitrile (1 mg, 2.307 mumol, 82% yield) as a yellow powder.1H NMR (500 MHz, MeOD) delta 8.87 (s, 1 H), 8.59 (s, 1 H), 7.75 (s, 1 H), 7.33 (d, 2H, J = 8.5 Hz), 7.21 (s, 1 H), 7.07 (d, 2H, J = 8.5 Hz), 3.86 (s, 3H), 3.44 (d, 2H, J = 19.5 Hz), 3.08- 2.93 (m, 4H), 1.96-1.69 (m, 4H). LCMS (4) Rt = 1.62 min; m/z (ESI+) 434 (MH+).

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

Reference:
Patent; CANCER RESEARCH TECHNOLOGY LIMITED; WO2009/44162; (2009); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 113305-94-5, name is 5-Aminopyrazine-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 113305-94-5, category: Pyrazines

2- (2-Amino-4-methyl- phenoxymethyl) -morpholine-4-carboxylic acid tert-butyl ester (0.087 g, 0.270 mmol) was prepared from 2-amino-4- methyl-phenol according to methods of Compound 3, Steps 1 EPO and 2 using 2-hydroxymethyl-morpholine-4-carboxylic acid tert-butyl ester (prepared according to the procedure for Compound 2, Step 1 using the corresponding acid) and 4- methyl-2-nitro-phenol. It was combined with tr+/-phosgene (0.029 g, 0.10 mmol) , toluene (2 mL) and Hunig’s base(0.15 mL, 0.86 mmol), and stirred at room temperature for 25 min. The suspension then was transferred through a cannula to a cold solution (-780C) containing 5-amino- pyrazine-2-carbonitrile (0.032 g, 0.27 mmol), and lithium bis (trimethylsilyl) amide (0.27 mmol) in THF (1 mL) , which had been stirring at -78C for 30 min. The reaction was allowed to warm, then was stirred for 16 h at room temperature. A precipitate formed and was collected by- filtration to yield the desired product (0.043 cj).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 5-Aminopyrazine-2-carbonitrile, and friends who are interested can also refer to it.

Reference:
Patent; ICOS CORPORATION; WO2006/105262; (2006); 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. 113305-94-5, name is 5-Aminopyrazine-2-carbonitrile, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 113305-94-5

Palladium (II) acetate (39 mg, 0.17 mmol) was added to (+/-)-2,2″-bis(diphenylphosphino)- 1 ,1″-binaphthalene (321 mg, 0.51 mmol) in DMF/toluene (1/1 15 mL) and the resulting mixture was degassed under a stream of nitrogen gas for 10 min. 2-Amino-5- cyanopyrazine (210 mg, 1.7 mmol), sodium ferf-butoxide (250 mg, 2.6 mmol) and tert- butyl 3-((2-bromo-5-nitropyridin-4-yiamino)methyl)piperidine-1-carboxylate (713 mg, 1.7 mmol) were added and the mixture was degassed for a further 5 minutes then heated at 150 C for 30 min using microwave irradiation. The mixture was concentrated in vacuo and water and ethyl acetate were added. The aqueous phase was extracted three times with ethyl acetate. The combined organic phases were dried (Na2SO4) and concentrated. The residue was purified by flash column chromatography on silica, eluting with a gradient of ethyl acetate in hexane, 10 – 100% over 50 min. The fractions containing the product contaminated with 2-amino-5-cyanopyrazine were combined, evaporated and repurified by silica column chromatography, eluting with a gradient of ethyl acetate in hexane, 10 – 50% over 45 min. Tert-butyl 3-((2-(5-cyanopyrazin-2-ylamino)-5-nitropyridin- 4-ylamino)methyl)piperidine-1-carboxylate was obtained as a yellow solid (265 mg, 34%).LCMS (1): Rt = 2.38 min; m/z (ESI+) 455 (MH+). 62

According to the analysis of related databases, 113305-94-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; CANCER RESEARCH TECHNOLOGY LIMITED; WO2009/44162; (2009); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Some common heterocyclic compound, 113305-94-5, name is 5-Aminopyrazine-2-carbonitrile, molecular formula is C5H4N4, 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: 113305-94-5

2-Amino-5-cyano pyrazine (0.25 g, 2.08 mmol) was dissolved in a mixture of 3:1 THF and DCM (40 mL) and pyridine (0.49 g, 6.2 mmol) was added. The mixture was stirred for 15 minutes then phenylchloroformate (0.97 g, 6.2 mmol) was added and the reaction mixture was heated at 50C for 2 hours. The reaction mixture was allowed to cool to room temperature then DCM (40 mL) and water (25 mL) were added. The separated organic layer was washed with water (2 x 25 mL), brine (25 mL), dried (Na2S0 ) and the solvents removed under reduced pressure to give the title compound (0.8 g) which was used without further purification.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 113305-94-5, its application will become more common.

Reference:
Patent; SENTINEL ONCOLOGY LIMITED; BOYLE, Robert George; BOYCE, Richard Justin; WO2013/72502; (2013); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 113305-94-5,Some common heterocyclic compound, 113305-94-5, name is 5-Aminopyrazine-2-carbonitrile, molecular formula is C5H4N4, 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 1; 5-Isothiocyanatopyrazine-2-carbonitrile; A solution of thiophosgene (1.86 g, 15 mmol) in THF (4 mL) is added dropwise to a solution of 5-aminopyrazine-2-carbonitrile (1.20 g, 10 mmol) and pyridine (2 mL) in CH2CI2 (200 mL) and THF (25 mL) at room temperature. The reaction mixture is stirred at room temperature for 3 h. The mixture is concentrated and the crude product is diluted with ethyl acetate, filtered and concentrated to give the title compound.

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

Reference:
Patent; ELI LILLY AND COMPANY; FAROUZ, Francine, S.; HOLCOMB, Ryan, Coatsworth; KASAR, Ramesh; MYERS, Steven, Scott; WO2010/77758; (2010); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem