Tag: M.W=100-200

Synthetic Route of 16298-03-6, 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. 16298-03-6, name is Methyl 2-aminopyrazine-3-carboxylate, This compound has unique chemical properties. The synthetic route is as follows.

1.5 equivalents of N-iodosuccinimide are added at room temperature to 5 g (32.7 mmol) of a methyl 3-aminopyrazine-2-carboxylate solution in 25 ml of dimethylformamide. The reaction medium is heated at 65°C for 1 hour, added together with 0.5 equivalents of N-iodosuccinimide and maintained at 65°C for 24 hours. After returning to room temperature, the solvent is evaporated and then the product is extracted several times with dichloromethane. The organic phases are combined, washed with 10percent sodium bisulfite solution, dried on magnesium sulfate and concentrated to yield 8 g (88percent) of methyl 3-amino-6-iodopyrazine-2-carboxylate in the form of a yellow solid. LCMS (EI, m/z): (M+1) 280 1H NMR: deltaH ppm (400 MHz, DMSO): 8.50 (1H, s, CHarom), 7.50 (2H, bs, NH2), 3.20 (3H, s, CH3)

The chemical industry reduces the impact on the environment during synthesis Methyl 2-aminopyrazine-3-carboxylate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; PIERRE FABRE MEDICAMENT; Sokoloff, Pierre; Cachoux, Frederic; EP2689778; (2014); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

36070-75-4, name is 5-Chloropyrazine-2-carbonitrile, 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. category: Pyrazines

A mixture of A-5 (500.00 mg, 3.58 mmol), [4- (trifluoromethoxy)phenyl]boronic acid (1.11 g, 5.37 mmol), Pd(i-Bu3P)2 (146.36 mg, 286.40 muiotaetaomicron) and K3P04 (1.52 g, 7.16 mmol) in dioxane (20 mL) and H20 (4 mL) was stirred at 80 C for 16 hours under N2. The mixture was concentrated to a residue, which was diluted with H20 (30 mL) and extracted with EtOAc (150 mL x 2). The combined organic phase was washed with water (50 mL x 2) and brine (50 mL), dried over Na2S04, filtered and concentrated to give a residue that was purified by flash chromatography on silica gel (EtOAc in PE = 5% to 10% to 15%) to give A-6 (520.00 mg, 1.96 mmol) as a solid. 1H NMR (400MHz, CDC13) = 9.14 (d, 1H), 8.96 (d, 1H), 8.16 (d, 2H), 7.41 (d, 2H).

The synthetic route of 36070-75-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PRAXIS PRECISION MEDICINES, INC.; REDDY, Kiran; MARTINEZ BOTELLA, Gabriel; GRIFFIN, Andrew, Mark; MARRON, Brian, Edward; (141 pag.)WO2018/98491; (2018); A1;,
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5521-58-4, name is 5-Methylpyrazin-2-amine, 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. category: Pyrazines

l-Chloro-N,N.2-trimethyl-prop-l -en- 1 -amine (0.26 mL, 2.0 mmol) was added to a solution 5 of 3-[(2S)-l-(difluoromethoxy)propan-2-yl]oxy-5-phenylmethoxy-benzoic acid (0.54 g,1.5 mmol) in DCM (20 mL) and stirred for 1 hour. 5-Methylpyrazin-2-amine (ClambdaS no.5521-58-4) (335 mg, 3.1 mmol) then pyridine (0.25 mL, 3.1 mmol) were added and the reaction stirred for a further 30 minutes before being reduced in vacuo and partitioned between ethyl acetate (50 mL) and water (50 mL). The aqueous layer was further extracted K) into ethyl acetate (50 mL) and the combined organics washed with water (50 mL), brine(50 mL), dried (MgSO4), and reduced in vacuo. The crude residue was chromatographed on silica, eluting with 40-100% ethyl acetate in isohexane, to give the desired compound(0.48 g).1H NMR delta (CDCl3): 1.39 (d, 3H), 2.58 (s, 3H), 3.96 – 4.05 (m, 2H), 4.63 – 4.70 (m, IH), 15 5.13 (s, 2H), 6.30 (t, I H), 6.78 (t, IH), 7.09 (t, IH), 7.16 (t, IH), 7.35 – 7.48 (m, 5H), 8.17(s, IH), 8.39 (s, IH), 9.58 (d, IH); m/z 444 (M+H)+

The synthetic route of 5521-58-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2008/50117; (2008); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application 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.

General procedure: To a solution of 2-amino-5-cyanopyridine (2b) (1190 mg, 10.0mmol) in tetrahydrofuran(100 mL), iodomethane (2.83 mL, 45.5mmol) was added andthe mixture was stirred at 0 C. The mixture was slowly addedto sodium hydride (60% in oil, 1440 mg, 36.0mmol) and stirredfor 12 h. To the reaction mixture was added methanol (20mL) to quench the reaction. Further, the reaction mixture wasdiluted with water and extracted with ethyl acetate (3 200mL). The combined organic layers were dried over Na2SO4,filtered, and the solvents were concentrated under reduced pressure.The obtained residue was purified by silica gel columnchromatography (hexane/ethyl acetate = 1/1) to yield dimethylamino 3b (1120 mg, 7.62mmol, 76%) as a dark brown solid.

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:
Article; Saito, Ryohei; Kuchimaru, Takahiro; Higashi, Shoko; Lu, Shijia W.; Kiyama, Masahiro; Iwano, Satoshi; Obata, Rika; Hirano, Takashi; Kizaka-Kondoh, Shinae; Maki, Shojiro A.; Bulletin of the Chemical Society of Japan; vol. 92; 3; (2019); p. 608 – 618;,
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Pyrazine | C4H4N2 – PubChem

Synthetic Route of 186534-02-1, 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. 186534-02-1, name is 3,5,6-Trimethylpyrazine-2-carbaldehyde belongs to pyrazines compound, it is a common compound, a new synthetic route is introduced below.

To a solution of 3,5,6-trimethylpyrazine-2-carbardehyde (4.51 g, 30.0 mmol), 2- methyl-2-butene (12.8 mL, 120 mmol), and sodium dihydrogen phosphate 78ehydrate (4.68 g, 30.0 mmol) in /ert-butanol (90 mL) and water (30 mL) was added 80% sodium chlorite (10.2 g, 90.0 mmol) portionwise at 0 C. After being stirred at room temperature for 50 min, the reaction mixture was poured into 2N aqueous hydrochloric acid. The mixture was extracted with chloroform and the organic layer was dried over sodium sulfate, filtrated and concentrated in vacuo to give 3,5,6- trimethylpyrazine-2-carboxylate. MS (ESI): m/z 165 (M-H).

The synthetic route of 3,5,6-Trimethylpyrazine-2-carbaldehyde has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MITSUBISHI TANABE PHARMA CORPORATION; KAWANISHI, Eiji; HONGU, Mitsuya; TANAKA, Yoshihito; WO2011/105628; (2011); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

59489-71-3, name is 2-Amino-5-bromopyrazine, 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-Amino-5-bromopyrazine

A mixture of 5-bromopyrazin-2-amme (2.Og, 11.56mmol) and sodium thiomethoxide(1.62g, 23.12mmol) in dry dimethyl formamide (29ml) was stirred and heated at 1000C under nitrogen for 20 hours. The solvent was removed in vacuo and the residue treated with distilled water. The aqueous solution was extracted with DCM (3 times). The organics were combined dried with anhydrous sulphate, filtered and evaporated to give the title compound as a brown solid (1.12g, 69%). NMR (CDCl3): 2.75 (s, 3H), 4.65 (s, 2H), 8.13 (s, IH), 8.2 (s, IH); m/z 142.

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

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2006/95159; (2006); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Some common heterocyclic compound, 109838-85-9, name is (R)-2-Isopropyl-3,6-dimethoxy-2,5-dihydropyrazine, molecular formula is C9H16N2O2, 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. name: (R)-2-Isopropyl-3,6-dimethoxy-2,5-dihydropyrazine

Step C – Synthesis of Intermediate Compound Int-7cTo a solution of (i?)-2-isopropyl-3,6-dimethoxy-2,5-dihydropyrazine (6.16 g, 33.4 mmol) in THF (60 mL) was added TBAI (617 mg, 1.67 mmol). The mixture was cooled to -78 °C and a solution of rc-BuLi (14.7 mL, 2.5M in hexanes, 36.75 mmol) was slowly added over 10 minutes. The reaction mixture was allowed to stir at -78 °C for 30 minutes, then Int-7b in THF (20 mL) was slowly added over 10 minutes. The reaction was allowed to stir at -78 °C for 2 hours then allowed to warmed to room temperature and allowed to stir for about 15 hours. The reaction was quenched by addition of MeOH (5 mL), concentrated in vacuo, water added (50 mL) followed by diethyl ether (50 mL) and the layers were separated. The organic layer was washed with water (2 x 50 mL) then dried over Na2S04, filtered and concentrated in vacuo to provide the crude product. Further purification by column chromatograpy on a 330 g ISCO Redi-Sep silica gel column using a eluent of CH2C12 with a gradient of 0-10percent EtOAc/hexanes afforded the desired product Int-7c as a light amber oil (8.65 g, 63percent). 1H NMR (CDC13) ? 4.07-3.99 (m, 1H), 3.94- 3.89 (m, 1H), 3.79-3.71 (m, 2H), 3.68-3.63 (m, 6H), 2.32-2.17 (m, 1H), 1.25-1.21 (m, 1H), 1.06-0.95 (m, 5H), 0.88 (s, 10H), 0.74-0.68 (m, 1H), 0.69-0.66 (m, 2H), 0.12-0.02 (m, 12H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 109838-85-9, its application will become more common.

Reference:
Patent; MERCK SHARP & DOHME CORP.; DWYER, Michael, P.; KEERTIKAR, Kartik, M.; ZENG, Qingbei; MAZZOLA, Robert, D., Jr.; YU, Wensheng; TANG, Haiqun; KIM, Seong Heon; TONG, Ling; ROSENBLUM, Stuart, B.; KOZLOWSKI, Joseph, A.; NAIR, Anilkumar Gopinadhan; WO2013/39876; (2013); 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 61892-95-3 as follows. COA of Formula: C6H8N2O

To a solution of (5-methylpyrazin-2-yl)methanol (500 mg, 4.028 mmol, commercial source: Combi- Blocks) in dichloromethane (20 mL), thionyl chloride (0.35 mL, 4.825 mmol, Commercial source: Avra) was added slowly at 0 C. The reaction mixture was allowed to reach 26 C and stirred for 16 h at the same temperature. Upon completion, the reaction mixture was concentrated under reduced pressure. The residue was neutralized with saturated sodium bicarbonate solution (20 mL) and extracted with ethyl acetate (3×20 mL). The combined organic solution was dried over Na2S04, filtered and the filtrate was concentrated under reduced pressure to afford 2- (chloromethyl)-5-methylpyrazine (500 mg, crude) as a brown liquid.1H NMR (400 MHz, CDCI3) delta 8.60 (s, 1 H), 8.43 (s, 1 H), 4.67 (s, 2H), 2.59 (s, 3H). MS m/z [M+H]+= 143.04

According to the analysis of related databases, 61892-95-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; ALEMPARTE-GALLARDO, Carlos; ENCINAS, Lourdes; ESQUIVIAS PROVENCIO, Jorge; (206 pag.)WO2019/34729; (2019); 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., Product Details of 56423-63-3

General procedure: In a conical flask (50mL), a mixture of aryl halide (1 mmol), phenyl boronic acid (1.2 mmol),triethylamine (1 mmol), [Aemim]Br (1ml) and [Gmim]Cl-Pd (II) (0.1mol%, 5 mg)was added and stirred at 25OC for a period as indicated in Table 5(The reaction was monitored by HPLC and TLC). The resulting heterogeneousmixture was extracted with ethyl acetate or diethyl ether (3x 5 mL). Theorganic phase was separated and dried over anhydrous Na2SO4and evaporated. Evaporation of the solvent gave the crud product residue whichwas further purified by flash chromatography using n-hexane/EtOAc to give thedesired coupling product in 82-94% isolated yields.

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:
Article; Karthikeyan, Parasuraman; Vanitha, Arumugam; Radhika, Pachaiappan; Suresh, Kannan; Sugumaran, Arunachalam; Tetrahedron Letters; vol. 54; 52; (2013); p. 7193 – 7197;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

4745-93-1, name is 5H-Pyrrolo[2,3-b]pyrazine, 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. Application In Synthesis of 5H-Pyrrolo[2,3-b]pyrazine

Step 8-Preparation of propane-1-sulfonic acid {2-fluoro-3-[hydroxy-(5H-pyrrolo[2,3-b]pyrazin-7-yl)-methyl]-phenyl}-amide (19); To propane-1-sulfonic acid (2-fluoro-3-formyl-phenyl)-amide (18, 50 mg, 0.42 mmol) in 0.8 mL of methanol, 5H-pyrrolo[2,3-b]pyrazine (3, 103 mg, 0.42 mmol) and potassium hydroxide (71 mg, 1.3 mmol) were added under an atmosphere of nitrogen. The reaction was stirred at room temperature for 48 hours, then poured into water and extracted with ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate, filtered and the filtrate concentrated under vacuum. The resulting material was purified by silica gel column chromatography eluting with 60% ethyl acetate in dichloromethane. Appropriate fractions were combined and concentrated under vacuum to provide the desired compound as a solid (19, 74 mg, 49%). MS (ESI) [M-H+]-=363.5.

The synthetic route of 4745-93-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Ibrahim, Prabha N.; Spevak, Wayne; Cho, Hanna; US2009/306087; (2009); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem