Category: 59489-71-3

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 59489-71-3 as follows. Product Details of 59489-71-3

EXAMPLE 1B 5-amino-2-pyrazinecarbonitrile A mixture of Example 1A (19.29 g, 105 mmol), freshly powdered KCN (16.9 g, 260 mmol), CuI (49.5 g, 260 mmol), 18-crown-6 (2.08 g, 7.8 mmol), and (PPh3)4Pd (1.8 g, 1.57 mmol) in N,N-dimethylformamide (600 mL) was stirred at room temperature for 30 minutes and heated to reflux in an oil bath preheated to about 200 C. The solution was stirred at reflux for 3 hours, cooled to room temperature, poured into ethyl acetate (1 L), filtered through diatomaceous earth (Celite), treated with silica gel (100 g), and concentrated. The concentrate was purified by flash column chromatography on silica gel with 60% ethyl acetate/hexanes to provide 11.9 g (94.4%) of the desired product. MS (APCI(+)) m/z 121 (M+H)+; 1H NMR (300 MHz, DMSO-d6) delta 8.40 (d, J=0.7 Hz, 1H), 7.90 (d, J=0.7 Hz, 1H), 7.47-7.69 (br s, 2H).

According to the analysis of related databases, 59489-71-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Li, Gaoquan; Li, Qun; Li, Tongmei; Lin, Nan-Horng; Mantei, Robert A.; Sham, Hing L.; Wang, Gary T.; US2004/259885; (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. 59489-71-3, name is 2-Amino-5-bromopyrazine, A new synthetic method of this compound is introduced below., name: 2-Amino-5-bromopyrazine

Step 1. A solution of 5-bromopyrazin-2-amine (4.53 g, 26.03 mmol), (4-isopropylsulfonylphenyl)boronic acid (7.125 g, 31.24 mmol) and K3PO4 (11.05 g, 52.06 mmol) in MeCN (90.60 mL)/Water (22.65 mL) was degassed with nitrogen. Pd[P(tBu)3]2. (665.4 mg, 1.302 mmol) was added and the degassing/flushing with nitrogen repeated. The reaction mixture was heated at 60 C. for 4 hours. A further 300 mg catalyst added over the next 30 min and the reaction mixture was stirred for 2 hours at 66 C. to give complete disappearance of the 5-bromopyrazine-2-amine starting material. The reaction mixture was cooled to ambient temperature and diluted with ethylacetate/water. The organic layer was separated and the aqueous layer extracted again with ethylacetate. The combined organic extracts were washed with aq NaCl/NaHCO3, dried over MgSO4, then filtered through a short silica gel column washing through with ethylacetate. The eluant was concentrated in vacuo to about 40 ml volume. The product was filtered off and the product washed with ethylacetate, petrol ether to give 5-(4-(isopropylsulfonyl)phenyl)pyrazin-2-amine a pale yellow powder (5.65 g, 78%). %). 1H NMR (400.0 MHz, DMSO-d6) delta 8.70 (s, 1H), 8.2 (d, 2H), 8.02 (s, 1H), 7.90 (d, 2H), 6.9 (s, 2H), 5.76 (s, 1H), 3.4-3.5 (m, 1H), 1.20 (d, 6H); LC/MS m/z 278.0 [M+H]+.

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; VERTEX PHARMACEUTICALS INCORPORATED; Charrier, Jean-Damien; Storck, Pierre-Henri; Pinder, Joanne; Studley, John R.; US2013/115312; (2013); 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. 59489-71-3, name is 2-Amino-5-bromopyrazine, A new synthetic method of this compound is introduced below., name: 2-Amino-5-bromopyrazine

Step 1: 2-amino-5-cyanopyrazine. To a stirred solution of 5-bromo-2-aminopyrazine (1.0 g) 5.8 mmol), CuI (2.76 g, 14.5 mmol), 18-crown-6 (121 mg; 0.46 mmol), potassium cyanide (943 mg; 14.5 mmol) in dimethylformamide (20 mL) was added Pd(PPh3)4 (196 mg; 0.17 mmol). After stirring at room temperature for 20 minutes the reaction was placed in an oil bath at 155 C. for 2 hours. The reaction was allowed to cool to room temperature and then poured into chloroform (300 mL). A precipitate formed that was filtered and triturated with hexanes to yield an off white solid (60% yield).

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; 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

Related Products 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.

Description 65: 2-bromo-5-iodopyrazine (D65); In a 1000 ml, ice bath cooled round-bottomed flask was dissolved 5-bromo-2-pyrazinamine D64 (11.3 g) in Acetonitrile (125 ml)/water (188 ml). In the mixture HI 67% water solution (45 ml, 401 mmol) was added. To the solution was added dropwise during 150 minutes a solution of sodium nitrite (31.4 g, 455 mmol) in water (125 ml). After the addition the reaction mixture was sealed, was let to warm-up to room temperature and was heated at 50 0C for 30 hours. After cooling the mixture was poured into 800 ml of 20% NaOH and was extracted with Et2O (3 x 800 ml). Gathered Et2O layers were washed with Na2S2Os saturated solution, dried over Na2SO4 and the solvent was evaporated. The crude was purified by Silica Chromatography (Biotage SP – column size 34Og) using DCM 100% to DCM/MeOH 90: 10 as eluent. It was recovered the title compound D65 (896 mg) as yellow powder. 1H NMR (400 MHz, CHLOROFORM-d) delta ppm 8.49 – 8.56 (m, 1 H) 8.65 (d, 1 H)

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; GLAXO GROUP LIMITED; AMANTINI, David; DI FABIO, Romano; WO2010/122151; (2010); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 59489-71-3, A common heterocyclic compound, 59489-71-3, name is 2-Amino-5-bromopyrazine, molecular formula is C4H4BrN3, 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.

Description 65: 2-bromo-5-iodopyrazine (D65); In a 1000 ml, ice bath cooled round-bottomed flask was dissolved 5-bromo-2-pyrazinamine D64 (11.3 g) in Acetonitrile (125 ml)/water (188 ml). In the mixture HI 67% water solution (45 ml, 401 mmol) was added. To the solution was added dropwise during 150 minutes a solution of sodium nitrite (31.4 g, 455 mmol) in water (125 ml). After the addition the reaction mixture was sealed, was let to warm-up to room temperature and was heated at 50 0C for 30 hours. After cooling the mixture was poured into 800 ml of 20% NaOH and was extracted with Et2O (3 x 800 ml). Gathered Et2O layers were washed with Na2S2Os saturated solution, dried over Na2SO4 and the solvent was evaporated. The crude was purified by Silica Chromatography (Biotage SP – column size 34Og) using DCM 100% to DCM/MeOH 90: 10 as eluent. It was recovered the title compound D65 (896 mg) as yellow powder. 1H NMR (400 MHz, CHLOROFORM-d) delta ppm 8.49 – 8.56 (m, 1 H) 8.65 (d, 1 H)

The synthetic route of 59489-71-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXO GROUP LIMITED; AMANTINI, David; DI FABIO, Romano; WO2010/122151; (2010); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 59489-71-3, name is 2-Amino-5-bromopyrazine, 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 59489-71-3, category: Pyrazines

5-Bromopyrazin-2-amine (5 g, 28.74 mmol), (4-isopropylsulfonylphenyl)boronic acid (7.866 g, 34.49 mmol) and K3P04 (12.20 g, 57.48 mmol) were combined in MeCN (100 mL) / Water (25 mL) and Pd[P(tBu)3]2 (734.4 mg, 1.437 mmol) was added. The reaction was heated at 60 C for 1 hour. The reaction mixture was cooled to ambient temperature and diluted with EtOAc and water. The layers were separated and the aqueous layer extracted with EtOAc (x 3). The combined organic layers were dried (MgS04), filtered andconcentrated in vacuo. The residue was triturated from DCM and isolated by filtration to give the sub-title compound as an orange solid (6.43 g, 76% Yield). 1H NMR (400.0MHz, DMSO) delta 1.17 (d, 6H), 3.43 (sept, 1H), 6.86 (s, 2H), 7.87 (d, 2H), 8.00 (s,1H), 8.20 (d, 2H) and 8.67 (s, 1H) ppm; MS (ES+) 278.2

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Reference of 59489-71-3,Some common heterocyclic compound, 59489-71-3, name is 2-Amino-5-bromopyrazine, molecular formula is C4H4BrN3, 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.

[0336] To 5-bromo-pyrazin-2-ylamine (0.46 g, 2.6 mmol), NaCN (1.3 g, 26 mmol) and CuCN (2.74g, 26 mmol) in a nitrogen-purged vial was added DMF (10 mL). The resulting mixture was heated at 12O0C over the weekend. After cooling down to room temperature, DMF was removed under high vacuum. The residue was partitioned between EtOAc and water. The organic extracts were combined, dried and concentrated to give the crude product as a yellow solid (0.296 g, 93%), which was used in the subsequent reaction 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 2-Amino-5-bromopyrazine, its application will become more common.

Reference:
Patent; LOCUS PHARMACEUTICALS, INC.; WO2008/8059; (2008); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Some common heterocyclic compound, 59489-71-3, name is 2-Amino-5-bromopyrazine, molecular formula is C4H4BrN3, 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: 59489-71-3

Preparation 10: 2-Bromo-5-iodopyrazineTo a solution of 5-bromopyrazin-2-amine (25.95 g, 147.13 mmol) in 1 ,2-dimethoxyethane (500 ml_) was added cesium iodide (38.75 g, 147.13 mmol), copper (I) iodide (8.52 g, 44.74 mmol) and iodine (18.93 g, 74.57 mmol). Isoamyl nitrite (120 ml_, 894.8 mmol) was then added dropwise via a dropping funnel and the reaction mixture was heated at 60 C for 1 hour. After this time, the mixture was cooled to room temperature and diluted with ethyl acetate (200 ml_), washed with ammonium chloride (sat. aq .200 ml_), then sodium thiosulphate (sat. aq.3 x 200 ml_). The organic layer was dried over MgS04, filtered and the solvent was evaporated under reduced pressure. The crude product was purified by silica column (heptane : ethyl acetate, 100:0 to 85:15) to give the title compound as a off-white solid (35.38 g).LCMS (run time = 5 minutes, System D): Rt = 2.09 minutes.H NMR (400 MHz, CDCI3): delta = 8.65 (s, 1 H), 8.50 (s, 1 H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 59489-71-3, its application will become more common.

Synthetic Route of 59489-71-3, These common heterocyclic compound, 59489-71-3, name is 2-Amino-5-bromopyrazine, 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.

C. 5-(4-(Triisopropylsilyloxy)phenyl)pyrazin-2-amine. Triisopropyl(4-(4,4,5, 5-tetramethyl-l,3,2-dioxaborolan-2-yl)phenoxy)silane (1.1 g, 2.9 mmol), 5- bromopyrazin-2-amine (507 mg, 2.9 mmol), dichloro[l,l’- EPO bis(diphenylphosphino)ferrocene]palladium(II) dichloromethane adduct (64 mg, 0.087 mmol), IM sodium carbonate (8.7 mL, 8.7 mmol), and dioxane (10 mL) were heated in a Biotage Emrys Optimizer microwave reactor at 120 C for 10 min. The reaction was extracted with water and ethyl acetate. The organic layer was dried over magnesium sulfate, filtered and concentrated. The resulting residue was purified using Biotage silica gel chromatography (0-100% ethyl acetate in hexanes) to give a tan solid (0.8 g, 80 % yield). 1H NMR (400 MHz, DMSCW6) delta 8.42 (s, IH), 7.92 (s, IH), 7.80 (d, J=8.6, 2H), 6.90 (d, J=8.6, 2H), 6.45 (s, 2H), 1.26 (q, J=IA, 7.2, 3H), 1.08 (d, J=7.4, 18H); MS (ESI) m/z 344.4 – [M+l]+.

Statistics shows that 2-Amino-5-bromopyrazine is playing an increasingly important role. we look forward to future research findings about 59489-71-3.

Reference of 59489-71-3, A common heterocyclic compound, 59489-71-3, name is 2-Amino-5-bromopyrazine, molecular formula is C4H4BrN3, 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.

EXAMPLE 2; 5-bromopyrazine-2-carbonitrile; i) Tetrakis (triphenyl phosphine) palladium(0) (10 mg) was added to a mixture of 5-bromopyrazin-2-amine (0.575 mmol), potassium cyanide (1.15 mmol), copper (I) iodide (0.575 mmol) and 18-crown-6 (20 mg) in dry DMF (1 mL) in a screw top reaction vessel under nitrogen atmosphere, and the mixture was heated with stirring at 200 C. for 1 h. After cooling, water (5 mL) was added and the product was extracted with chloroform (2¡Á) to give 5-aminopyrazine-2-carbonitrile after purification by chromatography (silica, hexane:ethyl acetate) (0.208 mmol, 36%).

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