Category: 59489-71-3

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., Safety of 2-Amino-5-bromopyrazine

19.1. 5-aminopyrazine-2-carbonitrile Heat a suspension of 1.85 g (20.7 mmol) of copper cyanide and 1 g (20.7 mmol) of sodium cyanide in 20 ml of DMF to 135 C., while stirring. Add 3.6 g (20.7 mmol) of 5-bromopyrazin-2-amine to the solution obtained, and maintain the temperature of 135 C. for 18 h. Then add 2 equivalents of sodium cyanide and of copper cyanide and continue heating for a further 24 h. After cooling, add 100 mL of 0.3N aqueous solution of sodium cyanide, stir the mixture for 1 h at 40 C., then distribute it in 300 mL of EtOAc/water 1:1 mixture. After washing with 2*100 mL of water, dry the organic phase over Na2SO4 and concentrate under reduced pressure. Purify the residue obtained by silica gel column chromatography, eluding with a cyclohexane/EtOAc gradient from 0 to 100% of EtOAc. After concentration under reduced pressure, we obtain 1.24 g of 5-aminopyrazine-2-carbonitrile in the form of oil. Yield=50%

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

Reference:
Patent; Sanofi Aventis; US2009/318473; (2009); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference 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.

Example 54 2 (R)- (3-CHLORO-4-METHANESULFONYL-PHENYL)-3-CYCLOPENTYL-N- [5- (L (S), 2-dihydroxy- ethyl)-pyrazin-2-yl]-propionamide [000276] This compound was prepared through a linear synthesis (Method A) and a convergent synthesis (Method B). Method A: [000277] A solution of 2-amino-5-bromopyrazine (500 mg, 2.87 mmol) in N, N- dimethylformamide (15 ML) was treated with tetrakis (triphenylphosphine) palladium (0) (66 mg, 0.06 MMOL), N, N-DIISOPROPYLETHYL AMINE (1.25 mL, 7.18 mmol), lithium chloride (426 mg, 0.06 mmol), and vinyltri-n-butyltin (840 L, 2.87 mmol), and the reaction was heated at 120C for 4 h. After such time, the reaction was cooled to 25C, treated with a saturated aqueous potassium fluoride solution (10 mL), and stirred at 25C overnight for 16 h. The solution was then diluted with methylene chloride (25 ML) and extracted with methylene chloride (3 x 15 mL). The combined organic layers were dried over sodium sulfate, filtered, and concentrated in vacuo. Biotage chromatography (FLASH 40S, Silica, 40/60 to 20/80 HEXANES/ETHYL acetate) afforded 2-amino-5-vinylpyrazine (211 mg, 61%) as a light yellow solid: EI-HRMS m/e calcd for C6H7N3 (M+) 121.0640, found 121.0642.

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; F. HOFFMANN-LA ROCHE AG; WO2004/52869; (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., Product Details of 59489-71-3

To the stirring solution of 2 (50 g, 287 mmol) in 1, 4-dioxane (1250 mL) was added 4- methoxycarbonyl phenyl boronic acid (2a) (56.89 g, 316 mmol) followed by 1M aqueous solution of potassium carbonate (575 mL, 574 mmol) at RT and purged with N2 gas for 40 minutes. Bis(triphenylphosphine)palladium(II)chloride (14.12 g, 20.12 mmol was added to the reaction mixture. The reaction mixture was heated to reflux temperature for 4h. After completion of the reaction (Confirm by TLC) the reaction mixture was cooled to RT and filtered through a bed of celite. The bed was washed with ethyl acetate (3 X 300 mL). Organic layer was separated and aqueous layer was re extracted with ethyl acetate (2 X 400 mL). The combined organic layer was washed with water, dried over sodium sulfate and concentrated under vacuum. The crude material was purified by column chromatography over silica gel (230-400 mesh) using 3.5% of MeOH in DCM as an eluent to afford 3 (39.1 g, 57%) as yellow solid.

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

Reference:
Patent; MMV MEDICINES FOR MALARIA VENTURE; UNIVERSITY OF CAPE TOWN; WATERSON, David; WITTY, Michael John; CHIBALE, Kelly; STREET, Leslie; GONZALEZ CABRERA, Diego; PAQUET, Tanya; (36 pag.)WO2017/9773; (2017); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application 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.

To a solution of 5-bromo-pyrazine-2-amine according to formula (ii) (2.3 g, 13.21 mmol) in 1,4-dioxane (15 ml) was added a boronic acid of formula (vi) such as 4- methylsulfonylphenylboronic acid (CombiBlocks) (2.77 g, 13.87 mmol) at RT and the resulting mixture was purged with N2 gas for 30 minutes. Bis(triphenylphosphine)palladium(II)chloride (463 mg, 0.66 mmol) and 1 M aqueous solution of potassium carbonate (15.84 ml, pre-purged with N2 gas) were added to the reaction mixture. The reaction mixture was heated to reflux for 16 h, cooled to RT and concentrated under vacuum. 10 ml of water was added to the reaction mixture and extracted with ethyl acetate (15 ml X 4). Combined organic layers were washed with brine solution (10 ml), dried over anhydrous Na2S04 and concentrated under vacuum. The crude material was purified by column chromatography over silica gel 230-400 mesh by using 2-3% of MeOH in DCM as an eluent to yield to a 5-substituted pyrazine- 2-amine of formula (vii) (2.5g, 75.91%) as white solid.

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

Reference:
Patent; UNIVERSITY OF CAPE TOWN; MMV MEDICINES FOR MALARIA VENTURE; YOUNIS, Yassir; CHIBALE, Kelly; WITTY, Michael, John; WATERSON, David; WO2013/121387; (2013); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route 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.

Sodium nitrite (1. 35 g, 19. 53 MMOL) was added portionwise to concentrated sulfuric acid (9. 8 mL) at 0 C. The mixture was heated at 50 C until all of the sodium nitrite had dissolved and the mixture was again cooled to 0 C. A solution of 5- BROMO-PYRAZIN-2-YLAMINE (2. 57 g, 14. 68 MMOL) in concentrated sulfuric acid (14. 7 mL) was added dropwise to the nitronium solution at 0 C. The ice bath was removed, the mixture warmed to ambient temperature and stirred for 15 minutes before heating to 45 C for seven minutes. After cooling to ambient temperature, the mixture was poured slowly with precaution into crushed ice water (100 mL). The aqueous phase was neutralized to pH 4 with 20% aqueous sodium hydroxide then extracted with ethyl acetate (3 x 100 mL). The combined organic extracts were washed with water (50 mL), dried (anhydrous magnesium sulfate), filtered, and evaporated to afford the title compound (1. 88 g, 73%) as a yellow solid. ‘H NMR (CDCl3, 300 MHz) ; 8. 07 (1 H, s), 7. 62 (1 H, D, J = 3. 0 Hz).

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; PFIZER INC.; WO2004/92145; (2004); 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. 59489-71-3, name is 2-Amino-5-bromopyrazine, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C4H4BrN3

5-Bromopyrazin-2-amine (0.11g, 0.63 mmol) was dissolved in NaOMe/MeOH (0.23g Na metal in 10 ml_ MeOH) and heated by microwave irradiation at 14O0C for 7 hours. After evaporation of the solvent, the residue was purified by preparative TLC, eluting with 30% ethyl acetate – n-hexane, to give 5-methoxypyrazin-2-amine (25 mg, 32%).1H NMR (500 MHz, MeOD) delta 7.64 (1H, s), 7.58 (1H, s), 3.85 (3H, s). LCMS (3) Rt 1.75 min; m/z (ESI+) 126 (MH+).

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 59489-71-3.

Reference:
Patent; CANCER RESEARCH TECHNOLOGY LIMITED; WO2009/44162; (2009); 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 59489-71-3 as follows. Recommanded Product: 59489-71-3

In a sealed tube, sodium methoxide (25 wt. %, 10 mL) was added to a suspension of 5-bromopyrazin-2-amine (1.12 g, 6.44 mmol) in MeOH (10 mL). The reaction was stirred at 100C for 40 h. At 15 h reaction time, reaction is about 40 % complete by LCMS. At 40 h reaction time, reaction is about 90% complete. After concentration the residue was taken up in EtOAc and extracted with brine, dried over sodium sulfate, concentrated and purified by flash chromatography on a 120 g silica gel cartridge with 30 to 50% EtOAc in hexane, 45 min, at 35 mL/min. Pure fractions were pooled, concentrated and dried under high vac to give 5-methoxypyrazin-2-amine (455 mg, 57 %).1H NMR (400 MHz, CDCl3) d ppm 7.75 (1 H, d, J=1.26 Hz), 7.55 (1 H, d, J=1.51 Hz), 4.12 (2 H, br. s.), 3.87 (3 H, s). LCMS (method K) tR, 0.55min., MH+ = 126.1.

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:
Article; Iwuagwu, Christiana; King, Dalton; McDonald, Ivar M.; Cook, James; Zusi, F. Christopher; Hill, Matthew D.; Mate, Robert A.; Fang, Haiquan; Knox, Ronald; Gallagher, Lizbeth; Post-Munson Amy Easton, Debra; Miller, Regina; Benitex, Yulia; Siuciak, Judy; Lodge, Nicholas; Zaczek, Robert; Morgan, Daniel; Bristow, Linda; Macor, John E.; Olson, Richard E.; Bioorganic and Medicinal Chemistry Letters; vol. 27; 5; (2017); p. 1261 – 1266;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

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.

Preparation c-120 5-Bromo-pyrazin-2-ol Sodium nitrite (1,35 g, 19.53 mmol) was added portionwise to concentrated sulfuric acid (9.8 mL) at 0 C. The mixture was heated at 50 C. until all of the sodium nitrite had dissolved and the mixture was again cooled to 0 C. A solution of 5-bromo-pyrazin-2-ylamine (2.57 g, 14.68 mmol) in concentrated sulfuric acid (14.7 mL) was added dropwise to the nitronium solution at 0 C. The ice bath was removed, the mixture warmed to ambient temperature and stirred for 15 minutes before heating to 45 C. for seven minutes. After cooling to ambient temperature, the mixture was poured slowly with precaution into crushed ice water (100 mL). The aqueous phase was neutralized to pH 4 with 20% aqueous sodium hydroxide then extracted with ethyl acetate (3*100 mL). The combined organic extracts were washed with water (50 mL), dried (anhydrous magnesium sulfate), filtered, and evaporated to afford the title compound (1.88 g, 73%) as a yellow solid. 1H NMR (CDCl3, 300 MHz): delta 8.07 (1H, s), 7.62 (1H, d, J=3.0 Hz).

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:
Patent; Pfizer Inc; US2005/187266; (2005); 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. 59489-71-3, name is 2-Amino-5-bromopyrazine, This compound has unique chemical properties. The synthetic route is as follows., name: 2-Amino-5-bromopyrazine

Example 17-7 Synthesis of 6-bromoimidazo[1,2-a]pyrazine A mixture of bromoacetaldehyde diethylacetal (19.7 g, 0.1 M) and 48% hydrobromic acid (4 ml) was heated to 140 C under nitrogen for 1.5 hours. The resulting mixture was poured onto a stirred suspension of sodium bicarbonate (40 g) in propan-2-ol (200 ml) and the resulting suspension was stirred for 10 minutes and then filtered. 5-Bromo-pyrazine-2-ylamine 12* (8.65 g, 0.05 M) was added to the filtrate and the resulting solution was heated at reflux for two hours. The solvent was evaporated in vacuo to give dark brown viscous material. The residue was treated with saturated sodium bicarbonate (150 ml) and extracted twice with dichloromethane (500 ml). The combined extracts were dried and evaporated in vacuo to give a brown oil, which was purified by flash chromatography with ethyl acetate as eluant to give 7.0 g of the desired product 16* as a light brown solid (Yield 71%). 1H-NMR (400 MHz, CDCl3): delta = 7.71 (s, 1 H, Ar), 7.85 (s, 1 H, ArH), 8.30 (s, 1 H, ArH), 8.92 (s, 1 H, ArH).

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 59489-71-3.

Reference:
Patent; Max-Planck-Gesellschaft zur Foerderung der Wissenschaften e.V.; Ullrich, Axel; Falcenberg, Mathias; EP2818471; (2014); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature 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.

2-amino-5-bromopyrazine (10g, 57m mol) and 1-bromo-2,2-dimethoxy-propane (15 g) were dissolved in I PA (30 ml_) and heated at 100 C in a sealed tube for 3 days. The reaction was quenched with sodium bicarbonate solution and filtered and extracted with ethyl acetate; the organic layer was dried over sodium sulphate and concentrated to give a brown solid that was used for the next step without further purification.

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; SALVENSIS; GARDNER, John Mark Francis; BELL, Andrew Simon; (78 pag.)WO2018/130853; (2018); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem