Pyrazines

Application of 5521-55-1,Some common heterocyclic compound, 5521-55-1, name is 5-Methylpyrazine-2-carboxylic acid, molecular formula is C6H6N2O2, 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.

General procedure: The corresponding pyrazinoic acid (5.0 mmol) was dispersed in dry toluene (20 mL) and mixed with 1.5eq. of thionyl chloride (0.55 mL, 7.5 mmol). The reaction mixture was heated to reflux for approximately 1 h. Next, the excess of thionyl chloride was removed by repeated evaporation with dry toluene under vacuum.The crude acyl chloride was dissolved in dry acetone(20 mL) and added drop-wise to a stirred solution of the corresponding aniline (5.0 mmol) with triethylamine(5.0 mmol) in dry acetone (30 mL). The reaction mixture was stirred at ambient temperature for up to 6 h. The completion of the reaction was monitored by TLC (eluent: hexane/ethyl acetate; r =2 : 1). The crude product adsorbed on silica gel by solvent evaporation was purified by flash chromatography(hexane/ethyl acetate gradient elution).The analytical data of the prepared compounds were fully consistent with the proposed structures and are available in the Supplementary Data.

The synthetic route of 5521-55-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Zitko, Jan; Barbora, Servusova-Vanaskova; Paterova, Pavla; Navratilova, Lucie; Trejtnar, Frantisek; Kunes, Jiri; Dolezal, Martin; Chemical Papers; vol. 70; 5; (2016); p. 649 – 657;,
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Synthetic Route of 1416740-16-3, These common heterocyclic compound, 1416740-16-3, name is 2-Bromo-7-nitro-5H-pyrrolo[2,3-b]pyrazine, 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.

Step 4: 2-bromo-5H-pyrrolo[2,3-b]pyrazin-7-amine[00200] To a solution of 2-bromo-7-nitro-5H-pyrrolo[2,3-b]pyrazine (21.76 g, 89.54 mmol) in acetic acid (108.8 mL) and concentrated hydrogen chloride (108.8 mL) was added dichlorotin dihydrate (101.0 g, 447.7 mmol). The reaction mixture was left to stir for 1 hour at ambient temperature. Reaction mixture was quenched by addition of 2M NaOH solution and the aqueous extracted with EtOAc (x3). Organic layer was dried (MgS04), filtered and concentrated in vacuo. The resulting solid was washed with saturated aHC03 solution and the solid collected, washed with water and dried to give 2-bromo-5H-pyrrolo[2,3-b]pyrazin- 7-amine. (10.4 g, 54.6%). XH NMR (400.0 MHz, DMSO) delta 1 1.50 (br s, 1H), 8.22 (s, 1H), 7.16 (s, 1H) and 4.35 (br s, 2H) ppm; MS (ES+) 214.79

The synthetic route of 1416740-16-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; MACCORMICK, Somhairle; STORCK, Pierre-henri; MORTIMORE, Michael, Paul; CHARRIER, Jean-damien; KNEGTEL, Ronald; YOUNG, Stephen, Clinton; PINDER, Joanne; DURRANT, Steven, John; WO2012/178123; (2012); A1;,
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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. 23611-75-8, name is Methyl 6-chloropyrazine-2-carboxylate, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C6H5ClN2O2

To a solution of 0.10 g of methyl 6-chloropyrazine-2-carboxylate in 2.9 mL of dioxane, 65 mg of 2-furanboronic acid, 74 mg of lithium chloride, 0.57 g of cesium carbonate, 21 mg of 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl and 24 mg of tris(dibenzylideneacetone)dipalladium(0) were added, and the mixture was heated under reflux for 2 hours. To the reaction mixture, water and ethyl acetate were added, the organic layer was separated, washed with a saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate, and the solvent was then distilled off under reduced pressure. The resultant residue was purified by flash silica gel column chromatography using gradient elution with hexane:ethyl acetate = 87:13 to 83:17 to obtain 74 mg of methyl 6-(2-furyl)pyrazine-2-carboxylate as a white solid. 1H-NMR (CDCl3) delta: 4.05 (3H, s), 6.60 (1H, dd, J = 3.5, 1.8 Hz), 7.30-7.32 (1H, m), 7.62-7.65 (1H, m), 9.12 (1H, s), 9.12 (1H, s)

According to the analysis of related databases, 23611-75-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; TOYAMA CHEMICAL CO., LTD.; Taisho Pharmaceutical Co. Ltd.; EP2022793; (2009); A1;,
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Pyrazine | C4H4N2 – PubChem

These common heterocyclic compound, 1379338-74-5, name is 5,7-Dichloropyrido[3,4-b]pyrazine, 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. Safety of 5,7-Dichloropyrido[3,4-b]pyrazine

To a solution of 4-hydroxycyclohexanone (171 mg, 1.5 mmol) in dloxane was added Cs2CO3 (488 mg, 1.5 mmol) and 5,7-dichloropyrido[4,3-b]pyrazine (200 mg, 1.0mmo) at room temperature. The mixture was stirred at 80 C for 18 hours. After that,the 5,7-dichloropyrido[4,3-b]pyrazine was consumed and the reaction was used for next step directly.

The synthetic route of 5,7-Dichloropyrido[3,4-b]pyrazine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; HUTCHISON MEDIPHARMA LIMITED; SU, Wei-Guo; DENG, Wei; WO2014/86032; (2014); A1;,
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Related Products of 122-05-4, 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. 122-05-4, name is Pyrazine-2,5-dicarboxylic acid, This compound has unique chemical properties. The synthetic route is as follows.

5 mmol of (2FPpy)2Ir(Cl)2Ir(2FPpy)2, 25 mmol of pyrazine-2,5-dicarboxylic acid (Py2CA), and 50 mmol of potassium carbonate were mixed in 100 mL of 1,2-dichloroethane, and refluxed for 24 hours under a nitrogen atmosphere. After the reaction was complete, the solution was cooled down to about 50 C., and filtrated. The filtrated solution was purified by using column chromatography to thereby produce (2FPpy)2Ir(Py2CA)Ir(2FPpy)2 at a yield of 86%.

The chemical industry reduces the impact on the environment during synthesis Pyrazine-2,5-dicarboxylic acid. I believe this compound will play a more active role in future production and life.

Reference:
Patent; SAMSUNG ELECTRONICS CO., LTD.,; US2008/269484; (2008); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 56423-63-3, 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. 56423-63-3, name is 2-Bromopyrazine belongs to pyrazines compound, it is a common compound, a new synthetic route is introduced below.

mixture of 3,3′,3″-(l,3,5,2,4,6-trioxatriborinane-2,4,6-triyl)tris(N-(4- (trifluoromethoxy)phenyl)benzamide) (Stage 5.1, 65 mg, 0.071 mmol), 2-bromopyrazine (63.6 mg, 0.4 mmol), Pd(PPh3)2Cl2 (8.42 mg, 0.012 mmol), Na2C03 (63.6 mg, 0.600 mmol), DME (299 muGamma), water (86 muGamma), and EtOH (42.8 mu) was stirred at 80C for 16 h. The RM was cooled, diluted with THF (4 mL), stirred for 2 h with Si-Thiol (Silicycle, 118 mg, 0.150 mmol), filtered and the filtrate was evaporated off under reduced pressure to give the crude product which was purified by flash chromatography (Redisep Silica gel column, 12 g, cyclohexane / EtOAc, from 20% to 75% EtOAc) to afford the title compound as white needles. UPLC-MS (Condition 1) tR = 2.66 min, m/z =360.0 [M+H]+, m/z =358.0 [M-H]”; XH-NMR (400 MHz, DMSO-d6) delta ppm 7.40 (d, J=8.6 Hz, 2 H) 7.67 – 7.77 (m, 1 H) 7.92 (d, J=9.0 Hz, 2 H) 8.08 (d, J=7.8 Hz, 1 H) 8.37 (d, J=7.8 Hz, 1 H) 8.67 – 8.71 (m, 2 H) 8.77 – 8.80 (m, 1 H) 9.38 (d, J=1.5 Hz, 1 H) 10.59 (s, 1 H).

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

Reference:
Patent; NOVARTIS AG; FURET, Pascal; GROTZFELD, Robert Martin; JONES, Darryl Brynley; MANLEY, Paul; MARZINZIK, Andreas; MOUSSAOUI, Saliha; PELLE, Xavier Francois Andre; SALEM, Bahaa; SCHOEPFER, Joseph; WO2013/171641; (2013); A1;,
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59303-10-5, name is 2-Chloro-5-methylpyrazine, 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: 59303-10-5

a reaction vessel 4-bromo-N-methylbenzamide (53.1 mg, 0.248 mmol), rac-1-((2S,3R,4R)-4- amino-2,3-dimethyl-6-(tetrahyd ro-2H-pyran-4-yl)-3,4-dihyd roquinolin- I (2H)-yl)ethanone (for apreparation see Intermediate 152, 37.5 mg, 0.124 mmol), sodium tert-butoxide (35.8 mg, 0.372 mmol), in 1,4-Dioxane (5 mL) were added. The solution was treated with Pd2(dba)3 (17.03 mg, 0.019 mmol) and DavePhos (9.76 mg, 0.025 mmol) and left to stir at 100 C for 2 h under N2. The reaction mixture was allowed to cool to rt and then filtered through celite and the celite washed with ethyl acetate. The combined filtrates were concentrated in vacuo to a crude orange/brown gum. This gumwas purified by MDAP (Formic) to give asolid. This solid was eluted through a NH2 SPE (5 g) with MeOH, the eluent was concentrated to give the product (17 mg, 0.039 mmol, 31.5%) as an off-white solid. LCMS (2 mm Formic): Rt = 0.83 mi [MH] = 436.

The synthetic route of 59303-10-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY (NO.2) LIMITED; AMANS, Dominique; ATKINSON, Stephen John; HARRISON, Lee Andrew; HIRST, David Jonathan; LAW, Robert Peter; LINDON, Matthew; PRESTON, Alexander; SEAL, Jonathan Thomas; WELLAWAY, Christopher Roland; WO2014/140076; (2014); A1;,
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Pyrazine | C4H4N2 – PubChem

Reference of 939412-86-9, A common heterocyclic compound, 939412-86-9, name is (3-Chloropyrazin-2-yl)methanamine hydrochloride, molecular formula is C5H7Cl2N3, 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.

To a solution of 3-(trifluoromethyl)-5,6,7,8-tetrahydro-[l,2,4]triazolo[4,3-a]pyridine-7- carboxylic acid (1.63 g, 6.93 mmol) in THF (35 mL) was added dropwise (COCl)2 (4.4 g, 34.66 mmol) and 0.1 mL of DMF at 0 C, the mixture was stirred at this temperature for 1 hours and then the solvent was removed. The resulting residue was dissolved in THF (35 mL), (3-chloropyrazin-2-yl)methanamine hydrochloride (1.37 g, 7.63 mmol) and DIEA(2.68 g, 20.79 mmol) was added, the mixture was stirred at 60 C for 1 h. Remove the solvent in vacuo and the residue was extracted with DCM and the combined organic layer was washed with water, brine and dried over anhydrous Na2S04. The organic layer was concentrated in vacuo and the residue was purified by silica gel column chromatography (DCM/THF= 100/20) to afford N-((3-chloropyrazin-2- yl)methyl)-3-(trifluoromethyl)-5,6,7,8-tetrahydro-[l,2,4]triazolo [4,3-a]pyridine-7- carboxamide (0.8 g, yield 32%). MS-ESI (m/z): 361 (M+l) + (Acq Method: 10-80AB_2min;Rt: 0.81 min)

The synthetic route of 939412-86-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SHARP & DOHME CORP.; WU, Hao; KIM, Ronald M.; LIU, Jian; LIU, Shilan; YANG, Chundao; ZHENG, Shuling; WO2014/113942; (2014); A1;,
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Pyrazine | C4H4N2 – PubChem

These common heterocyclic compound, 69214-33-1, name is 8-Chloroimidazo[1,2-a]pyrazine, 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. Recommanded Product: 69214-33-1

A cooled (0C) suspension of 8-chloroimidazo [1, 2-A] PYRAZINE (18.6 g, 0.12 mol) and sodium acetate (29.8 g, 0.36 mol) in methanol (125 ml, pre-saturated with solid potassium bromide) was treated with bromine (6.5 ml, 0.13 mol) added dropwise over 5 min. After stirring for 10 min thin-layer chromatography indicated no starting material. Solid sodium sulphite (15.3 g, 0.12 mol) was then added to the slurry and stirring continued for 10 min. The mixture was then treated with saturated aqueous sodium hydrogencarbonate (650 ml) added in portions. This mixture was extracted with dichloromethane (2 x 350 ml). The organics were combined, dried over anhydrous magnesium sulphate, filtered and concentrated to afford 3-bromo-8-chloroimidazo [1, 2-A] PYRAZINE as a cream- coloured solid:

The synthetic route of 8-Chloroimidazo[1,2-a]pyrazine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SHARP & DOHME LIMITED; WO2004/41826; (2004); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 912773-24-1, 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 912773-24-1 as follows.

General procedure: In a 1000ml three-necked flask, equipped with mechanical stirring, Ar gas protection, adding 3-phenyl-6-chloroimidazo [1,2-a] pyrimidine (7.16 g (molecular weight: 229, 0.030 mol), p-bromophenyl boronic acid pinacol ester 9.1 g (molecular weight: 282, 0.032 mol), catalyst Pd (PPh3) 4 was used in an amount of 1.8 g (molecular weight 1154, 0.001556 mol), 120 ml of a sodium carbonate aqueous solution (2M), 300 ml of toluene and 150 ml of ethanol. Stirring reflux, with TLC monitoring reaction, reaction 3.5hs after the reaction is complete. Cooled, separated, evaporated to dryness, using column chromatography The eluent was eluted with 1: 3 ethyl acetate: petroleum ether to give 9.0 g of a pale yellow solid having a purity of 97.0% and a yield of 83.2%. The synthesis step was the same as the fourth step in Example 1,Except that 3-phenyl-6-chloroimidazo[1,2, a]pyrimidine was added Substituted with 6-bromoimidazo [1,2-A]pyrazine,(3-phenylcarbazole-9-yl) -6,6,12,12-tetramethyl-6,12-dihydroindeno [1,2-b ] Fluorene-2-boronic acid pinacol ester instead of raw materials, other raw materials and process unchanged, Compound 29 was obtained.

According to the analysis of related databases, 912773-24-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Gu’an Dingcai Technology Co., Ltd.; Li Yinkui; Tang Jinming; Fan Hongtao; (40 pag.)CN104650089; (2017); B;,
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Pyrazine | C4H4N2 – PubChem