Pyrazines

Application of 369638-68-6,Some common heterocyclic compound, 369638-68-6, name is tert-Butyl (5-methylpyrazin-2-yl)carbamate, molecular formula is C10H15N3O2, 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.

A. 5-methylpyrazin-2-amine; To a solution tert-butyl 5-methylpyrazin-2-ylcarbamate (1.5 g, 7.17 mmol) in CH2CI2 (20 ml) was added TFA (2.6 mL, 35.86 mmol). The reaction mixture was stirred for 4 hours at room temperature after which, it was concentrated under reduced pressure. The reaction mixture was diluted with CH2CI2 and neutralized with sai.NaHCOs solution. The organic layer was separated and the aqueous layer was extracted with CH2CI2. The combined organic extracts were washed with brine, dried over MgS04, celite filtered and concentrated under reduced pressure. The crude product was purified by flash chromatography using (30% to 50% Ethyl acetate/Hexane) as a solvent to afford title compound (580 mg, 74% yield). MS m/z : 110 [M+l] .

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route tert-Butyl (5-methylpyrazin-2-yl)carbamate, its application will become more common.

Reference:
Patent; DANA-FARBER CANCER INSTITUTE, INC.; GRAY, Nathanael, S.; WO2011/90738; (2011); A2;,
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. 4858-85-9, name is 2,3-Dichloropyrazine, A new synthetic method of this compound is introduced below., Recommanded Product: 4858-85-9

[00295] Step A: 4-(3-Chloropyrazin-2-yl)-l-naphthonitrileA mixture of 2,3-dichloropyrazine (2.98g, 2mmol), 4-(4,4,5,5-tetramethyl- l,3,2-dioxaborolan-2-yl)-l-naphthonitrile (0.558mmol, 2mmol) palladium tetrakis triphenylphoshine (0.069g, 0.06mmol) and aqueous sodium carbonate solution (2M, 3mL, 6mmol) in dioxane (7mL) was heated to 80C for 12 hours. The reaction mixture cooled to room temperature, washed with water, extracted with ethyl acetate and purified by chromatography to yield 4-(3-chloropyrazin-2-yl)-l-naphthonitrile (0.36g, 68%).

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; ARDEA BIOSCIENCES, INC.; OUK, Samedy; VERNIER, Jean-michel; GUNIC, Esmir; CHEN, Chixu; WO2011/159839; (2011); A2;,
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Pyrazine | C4H4N2 – PubChem

Related Products of 1379338-74-5, 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.

Intermediate 18: 1,1-Dimethylethyl (3S)-3-{r(7-chloropyridor3,4-6lpyrazin-5- yl)oxy1methyl)-1-piperidinecarboxylate; 1 , 1-Dimethylethyl (3S)-3-(hydroxymethyl)-1-piperidinecarboxylate (129mg, 0.600mmol) (Apollo Scientific Limited) was taken up in N,N-dimethylformamide (DMF) (3ml), treated with sodium hydride (23.99mg, 0.600mmol) and allowed to stir at room temperature for 20min, a yellow solution resulted. 5,7-dichloropyrido[3,4- £>]pyrazine (100mg, 0.500mmol) was added and the reaction was allowed to stir at room temperature for a further 1 h. The reaction was partitioned between EtOAc (50ml) and NH4CI (50ml). The organic layer was dried using a hydrophobic frit and concentrated to give a brown oil. This oil was purified on silica (25g) using a 0-40% EtOAc/cyclohexane gradient. The appropriate fractions were summed and concentrated to give the title compound as a yellow gum (91 mg).LCMS (Method B): Rt = 1.26min, MH+ = 378.88

Statistics shows that 5,7-Dichloropyrido[3,4-b]pyrazine is playing an increasingly important role. we look forward to future research findings about 1379338-74-5.

Reference:
Patent; GLAXO GROUP LIMITED; ATKINSON, Francis Louis; ATKINSON, Stephen John; BARKER, Michael David; DOUAULT, Clement; GARTON, Neil Stuart; LIDDLE, John; PATEL, Vipulkumar Kantibhai; PRESTON, Alexander G; SHIPLEY, Tracy Jane; WILSON, David Matthew; WATSON, Robert J; WO2012/123312; (2012); A1;,
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Pyrazine | C4H4N2 – PubChem

Electric Literature of 87486-34-8, A common heterocyclic compound, 87486-34-8, name is 3,5-Dibromo-1-methylpyrazin-2(1H)-one, molecular formula is C5H4Br2N2O, 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 17 A solution of the aminopyrazole (0.28 g, 2.5 mmol) and the dibromopyrazinone (0.74 g, 1.1 equiv) were heated to 120° C. in isopropanol for 1 h. The reaction mixture was cooled to RT, and the product was isolated by filtration (0.43 g, 57percent).

The synthetic route of 87486-34-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Roche Palo Alto LLC; US2010/4231; (2010); 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. 109-08-0, name is 2-Methylpyrazine, A new synthetic method of this compound is introduced below., Application In Synthesis of 2-Methylpyrazine

General procedure: A 25 mL Schlenk tube equipped with a magneticstirring bar was charged with2,6-lutidine (0.75 mmol, 3equiv.), p-nitro-benzaldehyde(0.25 mmol), dioxane/water(1:1, 1ml) and [Hmim][H2PO4](1equiv.).The tube was sealed and heated at 100 for 24h. Aftercompletion of the reaction, the resulting solution was extracted with ether (3×10 ml). The organic layer was dried with anhydrous Na2SO4,and concentrated under vacuum. The residue was chromatographed on a silica gelcolumn eluted with a mixture of petroleum ether and ethyl acetate (1:1) to givepure products (92percent).

The synthetic route of 109-08-0 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Zhang, Xue-Yan; Dong, Dao-Qing; Yue, Tao; Hao, Shuang-Hong; Wang, Zu-Li; Tetrahedron Letters; vol. 55; 40; (2014); p. 5462 – 5464;,
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Pyrazine | C4H4N2 – PubChem

622392-04-5, name is 2-Bromo-5-iodopyrazine, 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. name: 2-Bromo-5-iodopyrazine

Preparation of compound 22a: 2-(2,2-difluoroethoxy)-5-iodopyrazineTo a solution of 2,2-difluoroethanol (0.74 g, 8.7 mmol) in THF (5OmL) at room temperature was added sodium butoxide (1.13 g, 11.4 mmol) and stirred for 15 min. The reaction mixture was cooled to 0 0C and a solution of 2-bromo-5-iodopyrazine (2.5 g, 8.7 mmol) in THF (50 ml_) was added slowly over 5 min. The reaction mixture was allowed to warm to room temperature and stirred for 16 h. The mixture was diluted with ethyl acetate and washed with sat. NH4CI. The organic layer was dried over MgSO4, filtered and concentrated which gave the title compound 22a (2.3 g, 90%).

The synthetic route of 622392-04-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PFIZER INC.; NINKOVIC, Sacha; BRAGANZA, John Frederick; COLLINS, Michael Raymond; KATH, John Charles; LI, Hui; RICHTER, Daniel Tyler; WO2010/16005; (2010); A1;,
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Pyrazine | C4H4N2 – PubChem

Synthetic Route of 54608-52-5,Some common heterocyclic compound, 54608-52-5, name is 2-Hydrazinopyrazine, molecular formula is C4H6N4, 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 of (Z)-3-(3-(4-chloro-3,5-bis(trifluoromethyl)phenyl)-lH-l ,2,4-triazol-l- yl)-N’-(pyrazin-2-yl)acrylohydrazide: In a 50-mL, 3-necked, round-bottomed flask charged with a solution of (Z)-3-(3-(4- chloro-3,5-bis(trifluoromethyl)phenyl)-lH-l,2,4-triazol-l-yl)acrylic acid (0.8 g) in 1 : 1 EtOAc:THF (20 mL). The solution was cooled to -70 C and treated sequentially with 2- hydrazinopyrazine (0.275 g, 1.2 eq.), T3P (50% in EtOAc; 2.5 mL, 2.0 eq.) and DIPEA (1.44 mL, 4.0 eq.), added dropwise. The clear reaction mixture was stirred at -60C for 1 h before being concentrated under reduced pressure (25 C, 20 mm Hg) to afford crude compound. Purification by column chromatography using (60/120 mesh Si02, elution with 3-4% MeOH in CH2C12) afforded 0.30 g (yield: 30%) (Z)-3-(3-(4-chloro-3,5-bis(trifluoromethyl)phenyl)- lH-l ,2,4-triazol-l-yl)-N’-(pyrazin-2-yl)acrylohydrazide. 1H NMR (400 MHz, DMSO-d6) delta = 10.53 (s, 1H), 9.58 (s, 1H), 9.11 (s, 1H), 8.47 (s, 1H), 8.32 (s, 1H), 8.13 (s, 1H), 8.06 (s, 1H), 7.97 (s, 1H), 7.52-7.55 (d, J = 10.4 Hz, 1H), 6.08-6.1 1 (d, J = 10.4 Hz, 1H); LCMS for CnHnClFe yO [M+H]+ 478.76 found 478.1 (RT 2.64 min, purity: 100%).

The synthetic route of 54608-52-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; KARYOPHARM THERAPEUTICS, INC.; SANDANAYAKA, Vincent, P.; SHACHAM, Sharon; MCCAULEY, Dilara; SHECHTER, Sharon; WO2013/19548; (2013); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 14508-49-7, A common heterocyclic compound, 14508-49-7, name is 2-Chloropyrazine, molecular formula is C4H3ClN2, 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 B: Preparation of 2-Hydrazinylpyrazine.Under nitrogen atmosphere, 2-chloropyrazine (96 mL, 1073 mmol) was added dropwise to 35 wt aqueous hydrazine (544 mL, 6009 mmol) at 65 C over 1 h. After the addition, stirring was continued at 63-67 C for 16 h and the reaction mixture was let stand at room temperature for two days. The mixture was filtered to remove a small amount of precipitate, then extracted with 10% iPrOH/dichloromethane (5 x 250 mL). The combined organic extracts were dried (MgS04), filtered, then concentrated under reduced pressure. The resulting solid was triturated with isopropyl acetate (600 mL). The solid was collected by filtration, rinsed with isopropyl acetate, then dried in vacuo to give the title compound (60 g) as a pale yellow solid. LCMS m/z = 111.2 [M+H]+; lU NMR (400 MHz, DMSO- ) delta 4.21 (s, 2H), 7.70 (d, 7 = 2.8 Hz, 1H), 7.89 (s, 1H), 7.93 (dd, 7 = 2.8, 1.5 Hz, 1H), 8.10 (d, 7 = 1.5 Hz, 1H).

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; ARENA PHARMACEUTICALS, INC.; THATTE, Jayant; BLACKBURN, Anthony C.; HAN, Sangdon; JONES, Robert M.; JUNG, Jae-Kyu; MONTALBAN, Anthony Garrido; PAL, Biman B.; RUETER, Jaimie Karyn; STRAH-PLEYNET, Sonja; THORESEN, Lars; XIONG, Yifeng; YUE, Dawei; ZHU, Xiuwen; WO2012/116279; (2012); A1;,
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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. 109838-85-9, name is (R)-2-Isopropyl-3,6-dimethoxy-2,5-dihydropyrazine, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 109838-85-9

Step 1: Synthesis of Intermediate 1-4.1R8 (212 g, 1151 mmol) in tetrahydrofuran (dry) (600 mL) is cooled to -78°C. Then n-butyllithium(2.5 M in hexanes, 552 mL, 1381 mmol) is added dropwise, keeping the temperature below -78°C.After 30 mm R9 (324g, 1209 mmol) in tertahydrofuran (dry) (120 mL) is added dropwise. Thereaction mixture is stirred at -78°C for 1 h. The mixture is quenched with saturated NH4C1 solutionand extracted three times with ethyl acetate. The organic layer is washed with brine, dried overNa2SO4 and evaporated in vacuo. The residue is purified by flash chromatography (heptane/ ethyl acetate = 80/20). Yield 60percent.

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 109838-85-9.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; ANDERSKEWITZ, Ralf; GRAUERT, Matthias; GRUNDL, Marc; OOST, Thorsten; PAUTSCH, Alexander; PETERS, Stefan; WO2014/140091; (2014); 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. 56423-63-3, name is 2-Bromopyrazine, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 2-Bromopyrazine

General procedure: Method S Parallel preparation of Examples 39-40: To a set of vials containing the requisite aryl bromide (0.12 mmol) was added bis[(tetrabutylammonium iodide)copper(I) iodide] (3.9 mg, 0.0034 mmol), 1,10 phenanthroline (2.5 mg, 0.014 mmol) followed by Cs2C03 (68 mg, 0.21 mmol). The vials were capped and transferred into a glove box under an atmosphere of nitrogen. To each vial was added a solution of H2 (30 mg, 0.069 mmol) in dioxane (1.0 mL). The vials were capped and the mixtures were heated at 100 C with stirring overnight. After that time, the mixtures were allowed to cool to RT. To each vial was added water (2 mL) and DCM (2 mL). The mixtures were transferred to a set of fritted barrel filters. The organic layer from each mixture was drained into a clean vial. Additional DCM (1 mL) was added to each aqueous layer and the organic layer was again drained and combined with the previous organic extract. The solvent from the combined organic layers was removed in vacuo. The crude residues were dissolved in DMSO (1 mL) and filtered. The crude products were purified by mass triggered reverse phase HPLC using the following conditions: [column: Waters XBridge CI 8, 5muiotaeta, 19×100 mm; solvent gradient: 19-21% initial to 49-51% final MeCN (0.1% NH4OH) in water (0.1% NH4OH) 25 mL/min; 8 min run time] to afford Examples 39-40.

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 56423-63-3.

Reference:
Patent; MERCK SHARP & DOHME CORP.; DAI, Xing; CUMMING, Jared, N.; LIU, Hong; SCOTT, Jack, D.; (0 pag.)WO2016/85780; (2016); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem