Pyrazines

Synthetic Route of 762240-92-6,Some common heterocyclic compound, 762240-92-6, name is 3-(Trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine hydrochloride, molecular formula is C6H8ClF3N4, 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 triazole base 1 (0.75g, 3.3mmol) in acetonitrile (15mL) at 5AC was added triethylamine (0.96mL, 6.9mmol) followed by ethylmalonyl chloride (0.45mL, 3.5mmol) over 5min. After being stirred for lOmin the reaction mixture was allowed to self warm to EPO room temperature and stirred for a further 90min. The reaction mixture was diluted with ethyl acetate and washed with IN HCl(aq). The aqueous phase was back extracted with ethyl acetate and the organic phases combined, dried over MgSO4 and evaporated. The residue was purified on silica, eluting with ethyl acetate to give amide 2 (0.76g, 76%) as a yellow oil.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3-(Trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine hydrochloride, its application will become more common.

Reference:
Patent; PEAKDALE MOLECULAR LIMITED; MADDAFORD, Adrian; GLEN, Rebecca; LEESE, David, Paul; HART, Terance, William; WO2008/40974; (2008); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 622392-04-5,Some common heterocyclic compound, 622392-04-5, name is 2-Bromo-5-iodopyrazine, molecular formula is C4H2BrIN2, 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.

(l-((l-(Trifluoromethyl)cyclobutyl)methyl)piperidin-4-yl)methanol (0.88 g, 3.50 mmol) was dissolved in THF (30 mL). At 0C, NaH (0.13 g, 5.25 mmol) was added thereto. The mixture was stirred for 30 minutes. 2-bromo-5-iodopyrazine (1.09 g, 3.85 mmol) was added thereto, followed by stirring at 55C for 10 h. To the reaction mixture, water was added, and the mixture was extracted with EtOAc. The organic layer was washed with saturated brine aqueous solution, dried with anhydrous MgS04, and then concentrated under reduced pressure. The obtained product was used without further purification. (1.40 g, 87%, colorless oil).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Bromo-5-iodopyrazine, its application will become more common.

Reference:
Patent; CHONG KUN DANG PHARMACEUTICAL CORP.; KIM, Yuntae; LEE, ChangSik; CHOI, DaeKyu; KO, MooSung; HAN, Younghue; KIM, SoYoung; MIN, JaeKi; KIM, DoHoon; WO2015/80446; (2015); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

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. 109838-85-9, name is (R)-2-Isopropyl-3,6-dimethoxy-2,5-dihydropyrazine belongs to pyrazines compound, it is a common compound, a new synthetic route is introduced below. Quality Control of (R)-2-Isopropyl-3,6-dimethoxy-2,5-dihydropyrazine

A solution of (2R)-(-)-2,5-dihydro-3,6-dimethoxy-2-isopropylpyrazine (4.25 g, 23.1 mmol) in tetrahydrofuran (30 ml) was cooled to -78° C., then n-butyllithium (1.6 M in hexane, 15.1 ml, 24.2 mmol) was added and the mixture was stirred for 1 hour. A solution of ((R)-1-iodomethyl-propyl)-benzene (6.30 g, 24.2 mmol) in tetrahydrofuran (30 ml) was added dropwise over 30 min and the mixture was stirred overnight while being allowed to warm slowly from -70° C. to room temperature. The reaction was quenched by addition of saturated aqueous ammonium chloride solution and the mixture was extracted with ether. The organic layer was separated, washed with saturated brine, then dried over Na2SO4 and concentrated in vacuo. The residue was purified by column chromatography (SiO2, heptane/EtOAc) to yield a light yellow oil (4.69 g, 64percent); MS (ISP): 317.0 ([M+H]+).

The synthetic route of 109838-85-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; HOFFMANN-LA ROCHE INC.; Hoener, Marius; Raab, Susanne; Risterucci, Celine; Sewing, Sabine; US9132136; (2015); B2;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

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. 5049-61-6, name is Pyrazin-2-amine belongs to pyrazines compound, it is a common compound, a new synthetic route is introduced below. SDS of cas: 5049-61-6

Step 1: Synthesis of 5-chloropyrazin-2-amine To a stirred solution of pyrazin-2-amine (3 g, 31.545 mmol) in anhydrous DCM (30 mL) was added NCS (4.2 g, 30.545 mmol) under nitrogen and stirred at 40 C. for 2 h. Progress of reaction was monitored by TLC. After reaction completion DCM was added and washed with water. The organic layer was dried over sodium sulphate and concentrated under reduced pressure. Crude was purified by silica gel (100-200 mesh) column chromatography using 20% ethyl acetate in hexane as eluent to yield 5-chloropyrazin-2-amine (0.59 g, 15%) as yellow solid. MS: 242.08 [M++1]

The synthetic route of 5049-61-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Mankind Pharma Ltd.; Patil, Rakesh Ishwar; Verma, Jeevan; Shah, Dharmesh; Ali, Sazid; Bapuram, Srinivasa Reddy; Rai, Santosh Kumar; Kumar, Anil; (146 pag.)US2017/291910; (2017); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 113305-94-5,Some common heterocyclic compound, 113305-94-5, name is 5-Aminopyrazine-2-carbonitrile, molecular formula is C5H4N4, 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.

5-Aminopyrazine-2-carbonitrile (5.45 mg, 0.045 mmol), Xantphos (1.749 mg, 3.02 mumol), tris(dibenzyiideneacetone)dipalladium(0) (1.384 mg, 1.511 mumol), and cesium carbonate (24.62 mg, 0.076 mmol) were added to tert-butyl 4-((2-chloro-5-(4-methoxyphenyl)pyridin- 4-ylamino)methyl)-4-fluoropiperidine-1-carboxylate (17 mg, 0.038 mmol) in a 0.2 mL microwave reaction vial. The vial was sealed and an inert atmosphere was introduced before dry dioxane (291 muL) was added. Nitrogen was bubbled through the mixture for 5 min. The mixture was heated at 150 0C for 1 hr by microwave irradiation. After cooling the mixture was diluted with 20% dichloromethane in MeOH and loaed onto a preparative thin layer chromatography plate. Elution with 50% EtOAc in hexane gave tert-butyl 4-((2-(5- cyanopyrazin-2-ylamino)-5-(4-methoxyphenyl)pyridin-4-ylamino)methyl)-4- fluoropiperidine-1-carboxylate (1.5 mg, 2.81 mumol, 7% yield) as a light yellow powder. LCMS (4) Rt = 2.35 min; m/z (ESI+) 534 (MH+). Trifluoroacetic acid (0.1 mL, 1.298 mmol) was added to tert-butyl 4-((2-(5-cyanopyrazin-2-ylamino)-5-(4-methoxyphenyl)pyridin-4- ylamino)methyl)-4-fluoropiperidine-1-carboxylate (1.5 mg, 2.81 mumol) dissolved in dichloromethane (0.5 mL) and the solution was stirred for 1 hr. The volatiles were removed in vacuo and the crude product was purified by ion exchange on lsolute SCX Il acidic resin (1 g), followed by preparative thin layer chromatography, eluting with 10% MeOH / 1% NH3 / 89% dichloromethane, to give 5-(4-((4-fluoropiperidin-4- yl)methylamino)-5-(4-methoxyphenyl)pyridin-2-ylamino)pyrazine-2-carbonitrile (1 mg, 2.307 mumol, 82% yield) as a yellow powder.1H NMR (500 MHz, MeOD) delta 8.87 (s, 1 H), 8.59 (s, 1 H), 7.75 (s, 1 H), 7.33 (d, 2H, J = 8.5 Hz), 7.21 (s, 1 H), 7.07 (d, 2H, J = 8.5 Hz), 3.86 (s, 3H), 3.44 (d, 2H, J = 19.5 Hz), 3.08- 2.93 (m, 4H), 1.96-1.69 (m, 4H). LCMS (4) Rt = 1.62 min; m/z (ESI+) 434 (MH+).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Aminopyrazine-2-carbonitrile, its application will become more common.

Reference:
Patent; CANCER RESEARCH TECHNOLOGY LIMITED; WO2009/44162; (2009); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Related Products of 21279-62-9, These common heterocyclic compound, 21279-62-9, name is 3-Chloropyrazine-2-carboxamide, 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.

General procedure: Compounds 1-6 were prepared according to conventional organic synthesis methods. 3-Chloropyrazine-2-carboxamide (1.27 mmol) was dissolved in THF (20 mL) in a round bottom flask and after that treated with two equivalents of the corresponding benzylamine and an equimolar amount of triethylamine. The reaction was conducted with continuous stirring and heating (70 C) under reflux in an oil bath for 15 h. Compounds 7-15 were synthesised using a microwave reactor with a focused field. 3-Chloropyrazine-2-carboxamide (1.27 mmol) was put into a thick-walled tube together with the corresponding benzylamine (2.54 mmol), pyridine (1.27 mmol), methanol (approx. 5 mL) and a magnetic stir bar and then sealed with a special cap. The reaction parameters were set according to the previously published paper as follows-140 C, 30 min, 200 W [29]. Reaction progress was checked by TLC (hexane:ethyl acetate-1:1). Regardless of the synthesis method used,all reaction mixtures were adsorbed on silica and subjected to preparative flash chromatography (hexane and ethyl acetate, gradient elution, detection wavelengths 260 nm and 280 nm). Products were recrystallized from ethanol or ethanol and water if necessary. All final substances were chemically characterized (1H-NMR, 13C-NMR, IR, melting point and elemental analysis).

Statistics shows that 3-Chloropyrazine-2-carboxamide is playing an increasingly important role. we look forward to future research findings about 21279-62-9.

Reference:
Article; Jandourek, Ondrej; Tauchman, Marek; Paterova, Pavla; Konecna, Klara; Navratilova, Lucie; Kubicek, Vladimir; Holas, Ondrej; Zitko, Jan; Dolezal, Martin; Molecules; vol. 22; 2; (2017);,
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. 16298-03-6, name is Methyl 2-aminopyrazine-3-carboxylate, A new synthetic method of this compound is introduced below., Safety of Methyl 2-aminopyrazine-3-carboxylate

In 20 ml of concentrated hydrochloric acid, 3.06 g (20 mmol, 1 eq.) of 3-amino-2-pyrazine methyl carboxylate is introduced at 0 C. A solution of 1.52 g (22 mmol, 1.1 eq.) of NaNO2 in 15 ml of water is then introduced drop by drop, while limiting the temperature to <5 C., until the gaseous emission stops. The solution obtained is filtered and added slowly to a sodium acetate solution (20 g) in 40 ml of water at 0 C. Stirring is maintained for 15 min, and then acidified with concentrated HCl. Extraction (4 times 30 ml of ethyl acetate) gives 1.35 g of chlorinated compound after drying and evaporation. NMR (1H, CDCl3): 4.05 (s; 3H; OCH3), 8.54 (d, J=2.4 Hz; 1H; arom. H), 8.60 (d, J=2.4 Hz; 1H; arom. 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; Imbert, Thierry; Monse, Barbara; Koek, Wouter; US2005/80085; (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. 486424-37-7, name is 3-Amino-6-bromopyrazine-2-carboxylic acid, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 486424-37-7

Triethylamine (0.48 mL, 3.44 mmol) was added to a mixture of 3-amino-6-bromo-2- pyrazinecarboxylic acid (0.25 g, 1.15 mmol; described in: Ellingson, R. C.; Henry, R. L. J. Am. Chem. Soc. 1949,2798-2800), 0- (BENZOTRIAZOL-1-YL)-NNN’, N’-TETRAMETHYLURONIUM tetrafluoroborate (0.405 g, 1.26 mmol) and 1-HYDROXYBENZOTRIAZOLE (0.17 g, 1.26 mmol) in N,N-dimethylformamide/acetonitrile, (1: 1, 5ML). After stirring for 0.5 h at room temperature, 3-methoxyaniline (0.15 ML, 1. 38 mmol) was added and the resulting mixture was stirred overnight at room temperature. Water (5-10 mL) was added and the precipitate was filtered off and washed with water to give 0.25 g (68% yield) of a yellow solid: MS (ESP) m/z 323,325 (M++1).

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 486424-37-7.

Reference:
Patent; ASTRAZENECA AB; WO2004/55006; (2004); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 875781-43-4, A common heterocyclic compound, 875781-43-4, name is 2-Bromo-5H-pyrrolo[2,3-b]pyrazine, molecular formula is C6H4BrN3, 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.

2-Bromo-5H-pyrrolo[2,3-b]pyrazine SM-1 (500 mg, 2.5 mmol), 1-Boc-4-(methylamino)piperidine SM-5a (1.082 g, 5.0 mmol), Pd2(dba)3 (139 mg, 0.1 mmol), DavePhos (238 mg, 0.6 mmol) and LiHMDS (12.625 mL, 12 mmol) are taken-up in dry THF (10 mL) and the resulting mixture is flushed with Argon and stirred for 1 h at 80 C. The reaction mixture is diluted with H2O and AcCN, Isolute is added, the solvent is removed in vacuo and the residue is purified via RP HPLC. The product containing fractions of IM-1a (HPLC-MS method A: tRet.=1.72 min; MS (M+H)+=332) are freeze dried.

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; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; Stadtmueller, Heinz; US2013/29993; (2013); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Some common heterocyclic compound, 22047-25-2, name is Acetylpyrazine, molecular formula is C6H6N2O, 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: Acetylpyrazine

Bromine (0.23 mL, 4.49 mmol) was added over 3 min. to a ~80C solution of 2- acetylpyrazine (0.50 g, 4.09 mmol) in 48% HBr (10 mL). The resulting mixture was heated between 80-90C for 1h, concentrated then reconcentrated again from acetone. Trituration of the resulting red-brown solid with ether/acetone (20 mL/5 mL) gave 0.94 g (82%) of 2-bromo- 1-pyrazin-2-yl-ethanone as a hydrobromide salt which had: NMR (DMSOd6) 9.12 (d, 1.2 Hz, 1 H), 8.89 (d, J = 2.5 Hz, 1 H), 8.78 (dd, J = 2.5, 1.7 Hz, 1 H), 8.07 br s, 1H + residual water), 4.96 (s, 2H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 22047-25-2, its application will become more common.

Reference:
Patent; PFIZER PRODUCTS INC.; WO2007/34277; (2007); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem