Category: 109-08-0

Application of 109-08-0,Some common heterocyclic compound, 109-08-0, name is 2-Methylpyrazine, molecular formula is C5H6N2, 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.

Compound 17: (E)-2-[2-(Pyrazin-2-yl)vinyl)benzamide hydrochloride: n-Butyl lithium (2.5 M in hexanes, 4.8 mL, 12.0 mmol, 1.2 eq.) was added dropwise to a solution of diisopropylamine (1.83 mL, 1.32 g, 13.0 mmol, 1.3 eq.) in dry tetrahydrofuran (25 mL) at -78 °C. The mixture was stirred at -78 °C for 10 min and 2-methylpyrazine (0.91 mL, 0.94 g, 10.0 mmol, 1.0 eq.) was added dropwise. The resulting mixture was stirred at -78 °C for 30 min. A solution of 2-cyanobenzaldehyde (1.31 g, 10.0 mmol, 1.0 eq.) in dry THF (10 mL) was added dropwise and the mixture was allowed to slowly warm up to room temperature over 2 h while stirring. The reaction was quenched by addition of water (20 mL). The pH was adjusted to -10 by careful addition of cone. HCl and the mixture was extracted with dichloromethane (3 x 25 mL). The combined organic extracts were washed with brine (25 mL), dried over sodium sulfate and evaporated in vacuo. The crude product was purified by column chromatography (SiO2, 1:9 methanol-ethyl acetate) providing 2-(1-hydroxy-2-(pyrazin-2-yl)ethyl)benzamide (1.06 g, 44percent yield) as a clear yellow oil. 1,8-Diazabicyclo[5.4.0]undec-7-ene (1.61 mL, 1.69 g, 11.1 mmol, 2.5 eq.) was dropwise to a stirred solution of 2-[1-hydroxy-2-(pyrazin-2-yl)ethyl]benzamide (1.00 g, 4.4 mmol, 1.0 eq.) in dichloromethane (25 mL). The mixture was stirred at room temperature for 16 h. Water (25 mL) was added and the layers were separated. The aqueous layer was extracted with dichloromethane (2 x 25 mL) and the combined organic extracts washed with brine (25 mL), dried over sodium sulfate and concentrated in vacuo. The residue was taken up in ethyl acetate (20 mL) and filtered. The solids were washed with ethyl acetate (2 x 5 mL) and dried in vacuo providing (E)-2-[2-(pyrazin-2-yl)vinyl]benzamide (0.21 g, 21percent yield) as a fine off-white solid. A solution of hydrochloric acid (2.0 M in diethyl ether, 0.53 mL, 1.07 mmol, 1.2 eq.) was added dropwise to a stirred suspension of (E)-2-[2-(pyrazin-2-yl)vinyl]benzamide (0.20 g, 0.09 mmol, 1.0 eq.) in dry diethyl ether (7.5 mL). The mixture was stirred at room temperature for 1 h and was filtered. The solids were washed with diethyl ether (2 x 5 mL) and dried in vacuo providing (E)-2-[2-(pyrazin-2-yl)vinyl]benzamide hydrochloride (0.20 g, 86percent yield) as a fine yellow solid; 1H NMR (400 MHz, DMSO-d6) delta 7.33-7.55 (m, 5H, 2Ar+NH2+C=CH), 7.88-7.96 (m, 2H, Ar), 8.11 (d, J = 16.0 Hz, 1H, C=CH), 8.51 (s, 1H, Ar), 8.64 (s, 1H, Ar), 8.71 (s, 1H, Ar).

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

Reference:
Patent; UNIVERSITY COLLEGE DUBLIN – NATIONAL UNIVERSITY OF IRELAND, DUBLIN; THE PROVOST, FELLOWS, FOUNDATION SCHOLARS, AND THE OTHER MEMBERS OF BOARD, OF THE COLLEGE OF THE HOLY AND UNDIVIDED TRINITY OF QUEEN ELIZABETH, NEAR DUBLIN; KENNEDY, Breandan; REYNOLDS, Alison; O’SULLIVAN, Jacintha; BAXTER, Andrew, Douglas; WO2015/107122; (2015); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 109-08-0, name is 2-Methylpyrazine, 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 109-08-0, Safety of 2-Methylpyrazine

In the glove box,Mn(CO)5Br (0.005mmol), [(E)-2-(2-(1-(2-pyridyl)ethylidene)-indenyl)pyridinium](0.006mmol),Add 1.0 mL of toluene,After stirring for two hours,Add 1a (2mmol),Benzyl alcohol 2b (1mmol),After the reaction at 135 C for 48 hours, the reaction was stopped.Evaporate the solvent,Column chromatography ethyl acetate / petroleum ether (1:10),Trans-disubstituted olefin derivative 3b.The product is a white solid.The yield was 63%.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 2-Methylpyrazine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Qingdao University of Science and Technology; Zhang Chunyan; (19 pag.)CN108250153; (2018); A;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 109-08-0, name is 2-Methylpyrazine, 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 109-08-0, Application In Synthesis of 2-Methylpyrazine

100L enamel reaction kettle, equipped with material dropping pipe (connected with metering pump), equipped with chlorine gas introduction pipe (connected with chlorine gas automatic control system), automatic pressure control system, temperature detection chain control system. Add 96kg of solvent dichloroethane and 1kg of triethylamine to the reaction kettle and start stirring, then pass chlorine gas, and set the pressure in the kettle to be automatically controlled at 0.02-0.03MPa for 20-30 minutes. Then start feeding with a metering pump at a rate of 5kg/h (according to 10kg of methylpyrazine mixed with 10kg of dichloroethane to be used evenly), the reaction exotherm is obvious, the reaction temperature is controlled at 45 ~ 60 C , the temperature is higher than 60C. The feeding system is automatically cut off at (if necessary, the water flow can be manually controlled to lower the temperature), the beating is completed in about 4 hours, and then the reaction is continued for 30 minutes at a pressure of 0.02 ~ 0.03MPa. Then lower the temperature to 30-40C, introduce the residual chlorine gas in the reaction kettle into the lye spray absorption tower to absorb, the remaining reaction liquid in the kettle is pressed into the dichloroethane turnover tank with nitrogen through the pipeline filter (containing chlorine gas for recycling), the reaction kettle The remaining chloropyrazine hydrochloride solid is dissolved in 30Kg of water first, and then neutralized with 30% alkaline solution to pH 6-7, and then separated into layers to obtain crude chloropyrazine, about 12Kg, content about 92 % Is directly used for the next reaction.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 2-Methylpyrazine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Shandong Jitian Biological Technology Co., Ltd.; Shandong Jitian Flavors Co., Ltd.; Yang Weixiang; Ren Wei; Yang Liang; Liu Shuzeng; Zhang Hongkui; Zhao Bin; Sun Yicheng; (6 pag.)CN110963974; (2020); A;,
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., Recommanded Product: 109-08-0

To a solution of methyl picolinate (1.14 g, 1 mL, 8.3 mmol) and 2-methylpyrazine (0.78 g, 0.76 mL, 8.3 mmol) in THF (15 mL) was added NaH (60% in mineral oil, 0.5 g, 12 mmol). The mixture was refluxed for 16 h. Once cooled to room temperature, the mixture was poured into saturated aqueous solution of NH4CI (30 mL) and extracted with EtOAc (3 x 30 mL). Organic fractions were combined, washed with brine (30 mL), dried over MgS04, and the solvent was evaporated in vacuo. The product, purified by column flash chromatography (CTHC^MeOH; 10: 1 to 5: 1), was obtained as a yellow solid (1.3 g, 80 %). (‘ 11 NMR shows a mixture of the keto- and enol- forms in ratio ca. 1 : 1) (0265) NMR (500 MHz, CDC13) (ppm) 13.65 (s, 1H), 8.71 (ddd, / = 0.9, 1.8, 4.8 Hz, 1H), 8.67 – 8.64 (m, 2H), 8.58 (d, J = 1.1 Hz, 1H), 8.52 (dd, J = 1.6, 2.6 Hz, 1H), 8.46 (d, J = 2.6 Hz, 1H), 8.36 – 8.31 (m, 2H), 8.12 – 8.05 (m, 1H), 8.00 – 7.94 (m, 1H), 7.88 – 7.83 (m, 1H), 7.83 – 7.77 (m, 1H), 7.50 (ddd, J = (0266) 1.2, 4.7, 7.5 Hz, 1H), 7.32 (ddd, / = 1.2, 4.7, 7.5 Hz, 1H), 6.94 (s, 1H), 4.80 (s, 2H); (0267) 13C NMR (126 MHz, CDC13) d (ppm) 197.7, 162.0, 154.2, 152.9, 152.6, 152.1, 149.3, 149.3, 146.3, (0268) 145.2, 144.4, 142.9, 140.2, 140.0, 137.2, 137.2, 127.7, 124.4, 122.5, 120.5, 94.2, 44.5; (0269) HRMS calcd for C11H10N3O [M+H]+ 200.0818, found 200.0816.

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; MASARYKOVA UNIVERZITA; PARUCH, Kamil; CARBAIN, Benoit; HAVEL, Stepan; DAMBORSKY, Jiri; BREZOVSKY, Jan; DANIEL, Lukas; SISAKOVA, Alexandra; NIKULENKOV, Fedor; KREJCI, Lumir; (190 pag.)WO2019/201865; (2019); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 109-08-0, These common heterocyclic compound, 109-08-0, name is 2-Methylpyrazine, 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.

A 2.5 M hexanes solution of n-BuLi (18.0 mL, 45 mmol) was added to a -78 °C THF solution (60 mL) of ^-BuOK (5.1 g, 45 mmol) and diisopropylamine (6.3 mL, 45 mmol). After 5 min at -78 °C the yellow mixture was warmed to -40 °C. Neat methylpyrazine (2.7 mL, 30 mmol) was added and the mixture rapidly turned dark red. After 30 min at -40 °C the mixture was cooled to -78 °C and neat allyl bromide (7.6 mL, 90 mmol) was added. After 30 min at -78 °C water was added and the mixture was partially concentrated to remove volatile organics. The resulting mixture was extracted with dichloromethane and the combined organics were dried (Na2SO4), concentrated, and purified via column chromatography to give 2.2 g of 2-but-3-enyl-pyrazine.

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

Reference:
Patent; JANSSEN PHARMACEUTICA NV; BARBAY, J., Kent; LEONARD, Kristi; CHAKRAVARTY, Devraj; SHOOK, Brian, Christopher; WANG, Aihua; WO2010/45012; (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;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application of 109-08-0, A common heterocyclic compound, 109-08-0, name is 2-Methylpyrazine, molecular formula is C5H6N2, 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.

In the glove box, Mn(CO)5Br (0.005mmol), [(E)-2-(2-(1-(2-pyridine)ethylidene)-indenyl)pyridine] (0.006 mmol),After adding 1.0 mL of toluene and stirring for two hours, 2-methylpyrazine 1a (2 mmol) was added.Benzyl alcohol 2e (1 mmol), after reacting at 135 ° C for 48 hours, the reaction was stopped, and the solvent was evaporated to dryness.Column chromatography ethyl acetate / petroleum ether (1:10),Trans-disubstituted olefin derivative 3e. The product was a white solid with a yield of 83percent.

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; Qingdao University of Science and Technology; Zhang Chunyan; (19 pag.)CN108250153; (2018); A;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 109-08-0,Some common heterocyclic compound, 109-08-0, name is 2-Methylpyrazine, molecular formula is C5H6N2, 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.

4-Bromobenzaldehyde (2.30 g, 12.5 mmol) and 2-methylpyrazine (1.17 g, 12.5 mmol)were dissolved in DMSO (7.5 mL). Powdered KOH (2.75 g, 50.0 mmol) was added and the reaction mixture was stirred atroom temperature for 8 h and then poured into 200 mL of water. The resulting precipitate was filtered and washed with water (2 x 150 mL). The crude product was crystallized from DCM/nheptaneto afford 10 (2.01 g, 62percent) as a brownish yellow solid. Mp:110-112 °C 1H NMR (300 MHz, CDCl3): delta (ppm): 7.14 (d, 1H,3J = 16.2 Hz), 7.45 (d, 2H, 3J = 8.7 Hz), 7.52 (d, 2H, 3J = 3.4 Hz), 7.68(d, 1H, 3J = 16.2 Hz), 8.42 (d, 1H, 3J = 2.4 Hz), 8.54 (dd, 1H,3J 2.4 Hz, 4J = 1.2 Hz), 8.62 (d, 1H, 4J = 1.2 Hz). 13C NMR (75 MHz, CDCl3): delta (ppm): 123.0 (C), 124.7 (CH), 128.7 (CH), 132.0 (CH), 133.9(CH), 135.0 (C), 143.0 (CH), 143.8 (CH), 144.4 (CH), 150.9 (C). IR (ATR) nu: 3048, 1487, 1403, 1009, 964 cm-1 HR-MS MALDI (matrix DHB):m/z calculated for C12H1079BrN2 [+M2H]+ 262.0095, found 262.0102.

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

Reference:
Article; Cvejn, Daniel; Achelle, Sylvain; Pytela, Old?ich; Malval, Jean-Pierre; Spangenberg, Arnaud; Cabon, Nolwenn; Bure?, Filip; Robin-Le Guen, Francoise; Dyes and Pigments; vol. 124; (2016); p. 101 – 109;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

109-08-0, name is 2-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: 2-Methylpyrazine

General procedure: 4-(Di-2-picolylamino)benzaldehyde (1) (110 mg, 0.36 mmol) and the appropriate methyldiazine derivative (0.72 mmol; 0.36 mmol for 4-methyl-2,6-dipyridin-2-yl-pyrimidine; 0.18 mmol for 4,6-dimethylpyrimidine) were dissolved in anhydrous THF (15 mL). KtBuO (1.44 mmol, 161 mg, 4 eq.) was slowly added at room temperature and the solution was heated under reflux for 15 h. The mixture was allowed to cool and water was added. THF was evaporated and the mixture was extracted with CH2Cl2. The organic layer was dried over MgSO4 and the solvent was removed under vacuum. The crude product was purified by flash chromatography.

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

Reference:
Article; Achelle, Sylvain; Rodriguez-Lopez, Julian; Bure?, Filip; Robin-Le Guen, Francoise; Dyes and Pigments; vol. 121; (2015); p. 305 – 311;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 109-08-0, name is 2-Methylpyrazine, 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 109-08-0, Product Details of 109-08-0

EXAMPLE 27 2-(hept-6-enyl)pyrazine (Compound ID 57) Methylpyrazine (940 mg, 912 10 mmol) was added to sodium amide (490 mg, 12.5 mmol) in 10 ml liquid NH3 at -65° C. and the red mixture was stirred for 30 min. A solution of 1-bromohex-5-ene (7.5 mmol) in dry ether was added dropwise and the mixture was stirred for another hour. The reaction was quenched by addition of ammonium chloride (626 mg, 11.7 mmol) and NH3 was evaporated by heating at ether reflux. The ether was removed and the residue extracted several times with ether. The combined ether phases were washed with water, dried over sodium sulfate, evaporated under vacuum and purified by FC (hexane/ethyl acetate 1/1). 2-(hept-6-enyl)pyrazine was isolated as a GC-pure oil (1.03 g, 78percent). Rf 0.52 (hexane/ethyl acetate 1/1). 1H-NMR (400 MHz, CDCl3): 8.48 (s, 1H); 8.45 (s, 1H); 8.39 (s, 1H); 5.78 (m, 1H); 5.00-4.94 (m, 2H); 2.81 (t, J=7 Hz, 2H); 2.04 (m, 2H); 1.75 (m, 2H); 1.41 (m, 4H). 13C-NMR (CDCl3): 158.29; 144.96; 144.34; 142.46; 139.22; 114.82; 35.81; 33.99; 29.65; 29.12; 29.03. GC-MS: 16.23 min, m/z 176.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 2-Methylpyrazine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Givaudan SA; US2010/113460; (2010); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem