Tag: M.W=100-200

6164-79-0, name is Methyl 2-pyrazinecarboxylate, 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. Product Details of 6164-79-0

To methyl pyrazine-2-carboxylate (3.35 g, 24.3 mmol) in EtOH (60 mL) was added calcium chloride (4.03 g, 36.4 mmol) followed by sodium borohydride (1.38 g, 36.4 mmol). The reaction mixture was stirred at 23C for 5 h. The mixture was quenched with a mixture of acetic acid (4.20 mL, 72.8 mmol) and water (1.31 mL, 72.8 mmol), and stirred for 30 min. The mixture was filtered through a pad a silica gel, and the pad was washed with 5-10% MeOH/DCM containing 0.3% conc. NH3 (aq). The combined filtrates were concentrated in vacuo, and the crude residue was purified by FCC (SiO2, elution with 0-10% MeOH/DCM)to provide 2.01 g (75%) of pyrazin-2-ylmethanol. 1H NMR (400 MHz, d6-DMSO): d ppm 8.71 (m, 1H), 8.56 (dd, 1H), 8.54 (d, 1H), 5.61 (t, 1H), 4.63 (d, 2H); LCMS (Method E): tR= 0.56 min, m/z 111.3 (M+H)+. Step 3: 2-(Chloromethyl)pyrazine

The synthetic route of 6164-79-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; VENENUM BIODESIGN LLC; LETOURNEAU, Jeffrey J; COLE, Andrew G; MARINELLI, Brett A; QUINTERO, Jorge G; (329 pag.)WO2017/214359; (2017); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 22047-25-2, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 22047-25-2 name is Acetylpyrazine, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

A 0.5 M solution of ethynylmagnesium chloride in tetrahydrofuran (31.90 mmol, Aldrich) is diluted with 50 ml of tetrahydrofuran and then cooled to 0 C. 3 g of 1-pyrazin-2-ylethanone (24.56 mmol, Lancaster) are then added in several fractions, and the mixture is stirred at 0 C. for 4 hours. The mixture is cooled once again with an ice bath and a solution of NH4Claq is added slowly. The mixture is extracted twice with ethyl acetate and the organic phases are then combined, dried over sodium sulphate, filtered, and concentrated under vacuum. The oily residue obtained is purified by silica chromatography (elution with a cyclohexane:ethyl acetate gradient, 70:30 to 50:50) and 2.9 g of the expected product are obtained in the form of a yellow oil (yield=80%).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Acetylpyrazine, and friends who are interested can also refer to it.

Reference:
Patent; SANOFI-AVENTIS; US2010/144757; (2010); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

These common heterocyclic compound, 22047-25-2, name is Acetylpyrazine, 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 Acetylpyrazine

General procedure: Previous method was used for preparing Ligands (L1-L7). Ethanol(10 mL, 1 mM) solution of piperidylthiosemicarbazide was added to corresponding aldehyde or ketone (one mole equivalent) and 5 drops of acetic acid glacial, with stirred and refluxed for 4 h. The precipitate was filtered with filter paper and rinsed with Cold ethanol. A vacuum desiccator was applied to dry the precipitate.

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

Reference:
Article; Qi, Jinxu; Yao, Qian; Qian, Kun; Tian, Liang; Cheng, Zhen; Wang, Yihong; Journal of Inorganic Biochemistry; vol. 186; (2018); p. 42 – 50;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Related Products of 108-50-9, These common heterocyclic compound, 108-50-9, name is 2,6-Dimethylpyrazine, 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 107 alpha,alpha’-Dichloro-2,6-dimethylpyrazine A stirred mixture of 2,6-dimethylpyrazine (55 mmol), N-chlorosuccinimide (110 mmol) and benzoylperoxide (1.0 mmol) in carbon tetrachloride (150 mL) is heated to reflux under nitrogen for 30 hours. Additional N-chlorosuccinimide (140 mmol) and benzoylperoxide (2.3 mmol) are added at 6 hours. The cooled reaction mixture is filtered and the filtrate washed with sodium carbonate (saturated aqueous solution) and dried. Evaporation of the solvent gives the title compound.

The synthetic route of 108-50-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ISIS Pharmaceuticals, Inc.; US6077954; (2000); A;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Related Products of 140914-89-2, A common heterocyclic compound, 140914-89-2, name is 2-(Pyrazin-2-yl)acetic acid, molecular formula is C6H6N2O2, 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-(9H-Carbazol-1-yl)aniline (50 mg, 0.194 mmol, 1 eq), 2-(pyrazin-2-yl)acetic acid (40 mg, 0.29 mmol, 1.5 eq) and DIPEA (162 muL, 0.929 mmol, 4.8 eq) were dissolved in DCM (2 mL, 0.1 M) and then had HATU (88 mg, 0.232 mmol, 1.2 eq) added before the solution was stirred for 16 h at room temperature. Upon reaction completion the crude mixture was concentrated onto silica gel before being purified by Isolera Biotage LPLC (CH/EA 8:2) to give 85 (32 mg, 0.084 mmol, 44%) as a white solid. Mpt: 189.0-191.0 C; vmax (cm-1) 3296, 1659, 1581, 1532, 1312, 1236, 738; 1H-NMR (400 MHz, CDCl3): deltaH 8.8 (br. s., 1 H), 8.3 (d, J=7.95 Hz, 1 H), 8.0 (m, 3 H), 7.8 (d, J=2.57 Hz, 2 H), 7.4 (m, 1 H), 7.3 (m, 5 H), 7.2 (m, 3 H), 3.5 (m, 2 H); 13C-NMR (100 MHz CDCl3): deltaC 166.6, 149.4, 144.1, 142.8, 142.6, 139.2, 137.6, 135.5, 130.9, 129.2, 128.9, 126.9, 126.3, 125.0, 123.4, 123.1, 122.4, 120.8, 120.3, 120.0, 119.8, 119.7, 110.7, 42.9; LR-ESI-MS: C24H19N4O [M+H]+ m/z found 379.25, cald 379.16.

The synthetic route of 140914-89-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Moustakim, Moses; Riedel, Kerstin; Schuller, Marion; Gehring, Andre P.; Monteiro, Octovia P.; Martin, Sarah P.; Fedorov, Oleg; Heer, Jag; Dixon, Darren J.; Elkins, Jonathan M.; Knapp, Stefan; Bracher, Franz; Brennan, Paul E.; Bioorganic and Medicinal Chemistry; vol. 26; 11; (2018); p. 2965 – 2972;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application of 4858-85-9,Some common heterocyclic compound, 4858-85-9, name is 2,3-Dichloropyrazine, molecular formula is C4H2Cl2N2, 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.

2,3-Dichloropyrazine A-1 (15 g; 100.68 mmol) and hydrazine hydrate 65% (15.509 ml; 201.37 mmol) are dissolved in 45 ml ethanol and stirred for 1 h at 80 C. While cooling down, a precipitate is formed. It is slurred up with a small amount of water and filtered off. It is washed with water and then dried to afford the product. Yield: 93% (13.6 g; 94.07 mmol) HPLC-MS: (M+H)+=145/147; tRet=0.34 min; method FECB5

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2,3-Dichloropyrazine, its application will become more common.

Reference:
Patent; ENGELHARDT, Harald; US2015/133447; (2015); 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. 27398-39-6, name is 3-Chloropyrazine-2-carboxylic acid, A new synthetic method of this compound is introduced below., Computed Properties of C5H3ClN2O2

To a suspension of sodium hydride (278 mg, 6.95 mmol, 60percent in oil) in DMF (10 mL) was added 1H-pyrazole (279 mg, 4.11 mmol) and the resulting mixture stirred at room temperature for 30 mins. 3-Chloropyrazine-2-carboxylic acid (500 mg, 3.16 mmol) was added and the mixture was heated to 60 °C for 2 h. After cooling to room temperature, water (20 mL) wasadded and the mixture extracted with 5percent MeOH in DCM (3 x 20 mL). The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated in vacuo to give Intermediate D as a solid. LRMS mlz (M+H) 191.0 found, 191.0 required.

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; MERCK SHARP & DOHME CORP.; KUDUK, Scott, D.; REGER, Thomas, S.; ROECKER, Anthony, J.; (0 pag.)WO2016/85783; (2016); 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. 108-50-9, name is 2,6-Dimethylpyrazine belongs to pyrazines compound, it is a common compound, a new synthetic route is introduced below. Product Details of 108-50-9

First, a synthesis method of an intermediate, 2-chloro-3,5-dimethylpyrazine is described. 7.12 g of 2,6-dimethylpyrazine and 6.5 mL of dimethylformamide (abbreviation : DMF) were put in a three-neck flask equiiped with a drop funnel and a thermometer, and the inside was refluxed under a nitrogen atmosphere. 6.7 mL of sulfuric chloride was put in a drop funnel and the reaction container was soaked in an ice bath. While the reaction solution was being stirred, the sulfuric chloride was dropped in such a way that the temperature of the solution be kept 45 C +/- 5 C. After that, water was added after it was confirmed that the temperature of the solution was 40 0C or lower. After it was confirmed again that the temperature of the solution was 40 0C or lower, an aqueous sodium hydroxide was added and the pH of the solution was adjusted to 7 to 8. This solution was subjected to steam distillation. The obtained solution was subjected to extraction using dichloromethane to separate an organic layer. The organic layer obtained was dried with magnesium sulfate. After the drying, the solution was filtrated. After the solvent of this solution was distilled off, the obtained residue was distilled under reduced pressure, so that an objective intermediate was obtained (clear and colorless liquid, yield of 36 %).

The synthetic route of 108-50-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SEMICONDUCTOR ENERGY LABORATORY CO., LTD.; WO2008/149828; (2008); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 939412-86-9, These common heterocyclic compound, 939412-86-9, name is (3-Chloropyrazin-2-yl)methanamine hydrochloride, 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 3: Synthesis of 3-(4-Fluorophenyl)-imidazo[l,5-a]pyrazine-8-carboxylic acid (3);To a suspension of 2-aminomethyl-3-chloropyrazine hydrochloride (900 mg, 5 mmol) in dichloromethane (25 mL) is added 4-fluorobenzoyl chloride (730 lL, 6.1 mmol) followed by DIPEA (2.0 mL, 11 mmol). After 1 day, the mixture is concentrated and diluted with saturated aqueous ammonium chloride and extracted with EtOAc (3 x 40 mL). The combined organic layers are washed with brine (3 x 25 mL), dried over magnesium sulfate, filtered and concentrated. The residue is passed through a pad of silica gel using dichloromethane-heptane (1: 1) to load the sample and then eluting with dichloromethane to afford N-(3-chloro-pyrazin-2-ylmethyl)-4-fluoro-benzamide as an oil which partially solidified.

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

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; COOK, Brian Nicholas; KUZMICH, Daniel; WO2011/56440; (2011); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 109838-85-9, name is (R)-2-Isopropyl-3,6-dimethoxy-2,5-dihydropyrazine, 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 109838-85-9, Product Details of 109838-85-9

(2R)-(?)-2,5-Dihydro-3,6-dimethoxy-2-isopropylpyrazine (212 g, 1151 mmol) in dry tetrahydrofuran (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 min 4-bromo-2-fluorobenzyl bromide (324 g, 1209 mmol) in dry tetrahydrofurane (120 mL) is added dropwise. The reaction mixture is stirred at ?78° C. for 1 h. The mixture is quenched with saturated NH4Cl solution and extracted three times with ethyl acetate. The organic layer is washed with brine, dried over Na2SO4, filtered and evaporated in vacuo. The residue is purified by flash chromatography (heptane/ethyl acetate=80/20). Yield 60percent.

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, (R)-2-Isopropyl-3,6-dimethoxy-2,5-dihydropyrazine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Boehringer Ingelheim International GmbH; VINTONYAK, Viktor; GRAUERT, Matthias; GRUNDL, Marc; PAUTSCH, Alexander; (64 pag.)US2016/75704; (2016); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem