Author: Jessica.F

Electric Literature of 22047-25-2, 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. 22047-25-2, name is Acetylpyrazine belongs to Pyrazines compound, it is a common compound, a new synthetic route is introduced below.

To a solution of 5-methyl-2-furaldehyde (24.59 mmol) and 2-acetylpyrazine (24.59 mmol)was added 20 mL of ethanol. The mixture was dissolved first before addition of 2% ethanolicKOH (9.63 mL) at 0C and stirred for 24 hr at 25C. After the completion of reaction wasmonitored by TLC, crushed ice was added to the reaction mixture. The precipitate formedwas filtered, washed with cold water, dried, and recrystallized by absolute ethanol. of 3-(5-methylfuran-2-yl)-1-(pyrazin-2-yl)prop-2-en-1-one (5) Yellow crystal (77.4% yield) m.p. 113.4-115.7C, IR (cm-1): 3104 (C-H aromatic), 2923 (CHaliphatic), 1662 (C=O), 1598 (C=C olefinic), 1558 and 1518 (C=C aromatic). 1H NMR(400 MHz, CDCl3): Table 1); 13C NMR (100 MHz, CDCl3): Table 1; Found (ESI): 215.0815[M+ H+], (C12H11N2O2 requires 215.0821).

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, Acetylpyrazine, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Mokhtar, Zakiah; Jamalis, Joazaizulfazli; Bohari, Siti Pauliena Mohd; Rosli, Mohd Mustaqim; Fun, Hoong-Kun; Molecular Crystals and Liquid Crystals; vol. 631; 1; (2016); p. 119 – 131;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application of 939412-86-9,Some common heterocyclic compound, 939412-86-9, name is (3-Chloropyrazin-2-yl)methanamine hydrochloride, molecular formula is C5H7Cl2N3, 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 (3S,7R,9aS)-3-methyl-4-oxooctahydropyrido[2,l- c][l ,4]oxazine-7-carboxylic acid (55 mg, 0.26 mmol) in anhydrous DCM (1 mL) was added oxalyl dichloride (0.068 mL, 0.77 mmol) in DCM (0.5 mL) at 0C under N2 atmosphere, and followed by 1 drop of DMF. The resulting mixture was stirred at 0C for 2 hrs. The reaction mixture was evaporated, dissolved with DCM (0.5 mL), and added to a solution of (3-chloropyrazin-2-yl)methanamine hydrochloride (56.1 mg, 0.31 mmol), and triethylamine (0.079 mL, 0.57 mmol) in DCM (1 mL), at 0C under N2 atmosphere, and the mixture was stirred for 12 hrs at 15 C.Then the mixture was diluted with DCM (5 mL), and H20 (5 mL). The organic layer was washed with brine (5 mL), dried over Na2S04, evaporated to get the crude product, which was then purified by prep-TLC (PE/THF=1 : 1) to give (3S,7R,9aS)-N-((3-chloropyrazin-2- yl)methyl)-3-methyl-4-oxooctahydropyrido[2, 1 -c] [ 1 ,4]oxazine-7-carboxamide (55 mg, yield: 62.9 %). 1H NMR (400MHz, CDC13) delta = 8.42 (d, J=2.5 Hz, IH), 8.29 (d, J=2.5 Hz, IH), 7.17 (br. s., IH), 4.76 – 4.57 (m, 2H), 4.16 (q, J=6.9 Hz, IH), 3.92 (dd, J=4.1 , 12.2 Hz, IH), 3.74 (dd, J=2.5, 12.0 Hz, IH), 3.37 – 3.25 (m, IH), 2.73 (t, J=12.3 Hz, IH), 2.42 (tt, J=4.0, 1 1.8 Hz, IH), 2.18 – 2.03 (m, 2H), 1.99 – 1.84 (m, IH), 1.79 – 1.68 (m, 2H), 1.44 (d, J=7.0 Hz, 3H).

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

Reference:
Patent; MERCK SHARP & DOHME CORP.; WU, Hao; KIM, Ronald M.; LIU, Jian; GAO, Xiaolei; BOGA, Sobhana Babu; GUIADEEN, Deodialsingh; KOZLOWSKI, Joseph; YU, Wensheng; ANAND, Rajan; YU, Younong; SELYUTIN, Oleg B.; GAO, Ying-Duo; LIU, Shilan; YANG, Chundao; WANG, Hongjian; WO2014/114185; (2014); 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 875781-43-4 as follows. Quality Control of 2-Bromo-5H-pyrrolo[2,3-b]pyrazine

General procedure: 2-Bromo-5H-pyrrolo[3,2-b]pyrazine(4; 0.471 g,2.39 mmol), 4-pyridylboronic acid (0.58 g, 4.72 mmol), dichloro 1,1′-bis(diphenylphosphino)ferrocenepalladium (II) dichloromethane adduct (0.097 g, 0.12 mmol), acetonitrile(3 mL) and 1M sodium carbonate (3 mL) were placed in a 10 mL CEM microwavevial. The vial was capped and irradiated in a CEM microwave reactor for 30minutes at 150 C.Water (3 mL) and ethyl acetate (9 mL) were added the layers were partitioned. Theaqueous layer was extracted with ethyl acetate (2 x 10 mL). The combined organicextracts were washed with saturated sodium chloride (5 mL), dried over MgSO4and concentrated under reduced pressure. The residue was purified by preparativereverse phase HPLC to give 2-(pyridin-4-yl)-5H-pyrrolo[2,3-b]pyrazine(14; 0.28 g,60%) as an off white solid: 1H NMR (400 MHz, DMSO-d6) delta 12.24 (s, 1H), 9.00(s, 1H), 8.69 (dd, J = 4.5, 1.6 Hz, 2H), 8.12 (dd, J = 4.5, 1.6Hz, 2H), 7.98 (d, J = 3.6 Hz, 1H), 6.74 (d, J = 3.6 Hz, 1H); ESMSm/z 197.1 (M+1).

According to the analysis of related databases, 875781-43-4, the application of this compound in the production field has become more and more popular.

Reference:
Article; Burdick, Daniel J.; Wang, Shumei; Heise, Christopher; Pan, Borlan; Drummond, Jake; Yin, Jianping; Goeser, Lauren; Magnuson, Steven; Blaney, Jeff; Moffat, John; Wang, Weiru; Chen, Huifen; Bioorganic and Medicinal Chemistry Letters; vol. 25; 21; (2015); p. 4728 – 4732;,
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. 19838-07-4, name is 3-Methylpyrazin-2(1H)-one, A new synthetic method of this compound is introduced below., Safety of 3-Methylpyrazin-2(1H)-one

To a solution of 3-methylpyrazin-2-ol (1.5 g, 13.62 mmol) in anhydrous DMF (20 mL) was added N-bromosuccinimide (2.67 g, 14.98 mmol) at 0 C. The reaction mixture was slowly warmed to room temperature and stirred overnight. The resulting mixture was poured into water, and extracted with IPA/DCM (1/5). The combined organics were dried over anhydrous Na2S04, filtered then concentrated. The residue was purified by column chomatography with 80% ethyl acetate/hexanes to give the title compound as white solid (1.97 g, 10.42 mmol, 77% yield).Exact mass calculated for C5H5BrN20: 188.0, found: LCMS m/z = 189.0 [M+H]+; lU NMR (400 MHz, DMSO-i ) delta ppm 2.27 (d, J = 0.5 Hz, 3H), 7.73 (s, 1H), 12.3 (s, 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.; JONES, Robert M.; HAN, Sangdon; BUZARD, Daniel J.; LEHMANN, Juerg; NARAYANAN, Sanju; YUE, Dawei; WO2011/127051; (2011); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 41110-33-2, name is Methyl 5-methylpyrazine-2-carboxylate, 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 41110-33-2, name: Methyl 5-methylpyrazine-2-carboxylate

EXAMPLE 3 The reaction is carried out, under nitrogen, in a 1 L¡Á4 neck flask equipped with a mechanical stirrer, water condenser (with gas inlet), and a thermocouple. The reactor is charged with 5-methylpyrazinecarboxylic acid, methyl ester (20.00 g), and methylene chloride (90 g). A solution of OXONE (84.67 g) in water (335 g) is added, and the mixture is vigorously stirred for 68 h at room temperature. The layers are separated, the organic layer is dried over magnesium sulfate, and gravity filtered. The aqueous layer is extracted with methylene chloride (3¡Á135 g). Each extract is poured through the filter containing the magnesium sulfate from above. The extracts are combined and the solvent is removed by distillation at 55 C. Residual solvent is removed under vacuum (25 inches of Hg at 55 C.) yielding 15.39 g (70%) of the n-oxide as an off-white solid).

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; ISP INVESTMENTS INC.; US2005/239803; (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. 36070-80-1, name is 5-Chloropyrazine-2-carboxylic acid, This compound has unique chemical properties. The synthetic route is as follows., SDS of cas: 36070-80-1

Oxalyl chloride (1.55 ml, 17.48 mmol), followed by DMF (2 drops), was added to a mixture of 5-chloropyrazine-2-carboxylic acid (2.31 g, 14.57 mmol) in DCM (40 ml). The reaction was stirred at RT for 2 hours after which time the volatiles were removed in vacuo. The residue was taken up DCM (40 ml) and azetidine (1.08 niL, 16.03 mmol) and triethylamine (4.46 ml, 32.06 mmol) added. The mixture was stirred at RT for 72 hours. The volatiles were removed in vacuo and ethyl acetate (100 ml) added to the residue. The organics were washed with water (100 ml), citric acid (50 ml), saturated sodium bicarbonate solution (50 ml), brine (50 ml), dried (MgSO4), filtered and the solvent removed in vacuo to give a yellow solid. The residue was chromatographed on silica, EPO eluting with a gradient of 50 -100% ethyl acetate in o-hexane, to give the desired compound as a yellow solid (2.38 g), 1H NMR delta (CDCl3): 2.35 – 2.42 (2H, m), 4.26 (2H, t), 4.67 (2H, t), 8.52 (IH, d), 9.09 (IH, d); m/z 198 (M+H)+.

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 36070-80-1.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2006/125958; (2006); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 1209646-17-2,Some common heterocyclic compound, 1209646-17-2, name is 5-(4-(tert-Butoxycarbonyl)piperazin-1-yl)pyrazine-2-carboxylic acid, molecular formula is C14H20N4O4, 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 suspension of I-77 (1.0 g, 3.53 mmol) in THF (20 ml) is added 1,1?-carbonyldiimidazole (0.63 g, 3.88 mmol) at room temperature. The mixture is stirred at 50 C. for 30 minutes. After this time I-19 (1.2 g, 3.88 mmol) is added as a THF solution (15 ml) and the resulting mixture is heated at 80 C. for 3 hours. The mixture is cooled and treated with AcOH (8 ml) then warmed to 80 C. and stirred over night. After this time the reaction is cooled to room temperature, concentrated and diluted with water. Extracted the product into DCM (2¡Á). The combined organics are washed with brine and dried (MgSO4). Filtered and concentrated. The remaining crude is purified via flash chromatography (silica gel, 0-5% MeOH/DCM) to afford I-84 (1.2 g).

The synthetic route of 1209646-17-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Boehringer Ingelheim International GmbH; BYLOCK, Lars Anders; US2013/195879; (2013); 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. 6966-01-4, name is Methyl 3-amino-6-bromopyrazine-2-carboxylate, A new synthetic method of this compound is introduced below., HPLC of Formula: C6H6BrN3O2

To a solution of 3-amino-6-bromo-pyrazine-2-carboxylic acid methyl ester (3g, 12.9 mmol) in DMF (40ml) was added 3-(hydroxymethyl)benzoic acid (2.16g, 14.22 mmol) followed by Et3N (2.7ml, 19.39 mmol) under nitrogen at room temperature. The mixture was stirred for 10 min before adding 1 ,1′-bis[dit- butylphosphino)ferrocene]paliadium chloride (0.25g, 0.039 mmol) and stirred overnight at 900C. The cooled reaction mixture was condensed. The residue dissolved in THF-EtOAc mixture (200ml, 1 :1), filtered to remove catalyst and evaporated. The filtrated was washed with brine, dried (MgSO4) and condensed. The resultant brown solid residue was subjected to flash column chromatography on silica eluting gradient of hexane to (3:1 , v/v) ethyl acetate and hexane to give title compound (1.61g, 48%) as a yellow/orange solid; LC/MS: Rt 1.74 (Method A) [M+H]+ 260.

The synthetic route of 6966-01-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; VERNALIS (R & D) LIMITED; WO2008/38010; (2008); 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 32111-21-0 as follows. Product Details of 32111-21-0

4.90 ml of tetrabutylammonium fluoride (1M solution in THF) are added to a solution of 500 mg (2.43 mmol) of iodopyrazine, 655 mg (3.64 mmol) of 4-fluoro-2-methoxy-1-prop-2-ynyloxy-benzene, 92 mg (0.48 mmol) of copper(l) iodide and 170 mg (0.24 mmol) ofbis(triphenylphosphine)palladium dichloride (Pd(PPh3)2CI2) in 16 ml of dioxane. The reactionmixture is stirred for 3 hours at 50C under an argon atmosphere and is then allowed to coolto 20C. The solvent is removed under reduced pressure and the crude product obtained ispurified by means of flash chromatography (eluant: ethyl acetate/petroleum ether 1/2). Thedesired title compound is obtained as a beige solid having a melting point of 88C in a yieldof 412 mg (66 % of theory).Rf = 0.28 in ethyl acetate/petroleum ether 1/2;1H NMR (CDCI3): delta(ppm)= 3.87 (s, 3H); 4.98 (s, 2H); 6.56-6.69 (m, 2H); 7.04 (dxd, J=5.6 and8.8 Hz, 1H); 8.48 (d, J=2.5 Hz, 1H); 8.52 (dxd, J=1.3 and 2.5 Hz, 1H); 8.62 (d, J=1.3 Hz,1H).

According to the analysis of related databases, 32111-21-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SYNGENTA PARTICIPATIONS AG; WO2003/104206; (2003); A2;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application of 32974-92-8, The chemical industry reduces the impact on the environment during synthesis 32974-92-8, name is 1-(3-Ethylpyrazin-2-yl)ethanone, I believe this compound will play a more active role in future production and life.

(1) 10 mmol of 2-acetyl-3-ethylpyrazine was dissolved in 20 ml of methanol,Stirring at 60 C for 15 min to prepare a solution;(2) taking 10 mmol of 4-methylthiosemicarbazide dissolved in 20 ml of methanol,The solution prepared in the step (1) is dropwise added to a methanol solution containing 4-methylthiosemicarbazide, and the reaction mixture is stirred under reflux at 60 C for 24 hours to obtain a pale yellow precipitate.After the reaction, the mixture was cooled to room temperature, poured into a beaker and evaporated, and the resulting precipitate was filtered.Wash 3 times with absolute ethanol,After drying, the ligand L2 is obtained;Yield: 86.7%,

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, 1-(3-Ethylpyrazin-2-yl)ethanone, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Guangxi Normal University; Yang Feng; Cai Meiling; Li Wenjuan; Liang Hong; (15 pag.)CN109796497; (2019); A;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem