Tag: M.W=100-200

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. 4774-14-5, name is 2,6-Dichloropyrazine, A new synthetic method of this compound is introduced below., HPLC of Formula: C4H2Cl2N2

General procedure: [Li(TMP)Zn(tBu)2] 1 was made according to the literature procedure2 on a 0.4 mmol scale in THF solution. To this solution 2-methoxypyridine (0.042 mL, 0.4 mmol) was added and the resultant light orange reaction allowed to stir at room temperature for 2 hours. Next the solution was cooled to 0C and quenched with I2 (508 mg, in 1 mL THF) and allowed to stir for 1 hour. Next a 10% solution of Na2S2O3 was added until bleaching and the product extracted with DCM (3 x 1 mL). The combined organic extracts were dried over MgSO4 and the solvent removed under reduced pressure. The residue was purified by SiO2 chromatography using Heptane:DCM as eluent (20:80–>40:60) to give 3-iodo2-methoxypyridine 2a as a colourless oil (87.1 mg, 92% yield).

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:
Article; Blair, Victoria L.; Blakemore, David C.; Hay, Duncan; Hevia, Eva; Pryde, David C.; Tetrahedron Letters; vol. 52; 36; (2011); p. 4590 – 4594;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 6705-33-5,Some common heterocyclic compound, 6705-33-5, name is Pyrazin-2-ylmethanol, molecular formula is C5H6N2O, 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-Fluoro-2-(pyrazin-2-ylmethoxy)nicotinic acid (211)To a solution of 2-chloro-5-fluoronicotinic acid (1.15g, 6.6mmol) in THF (20ml) under a N2 atmosphere was added 2-pyrazinylmethanol (l .Og, 9.2mmol) followed by a portion-wise addition of NaH (60% dispersion in mineral oil, 0.79g, 20mmol). The resulting suspension was stirred at room temperature for 2 d and then quenched with 1 M NaOH (10ml). After washing with DCM (x2), the aqueous layer was acidified with concentrated HC1 until the product precipitated out of solution (~ pH 5). The solids were filtered, washed with ?() and then dried under high vacuum to afford the title compound (0.5 lg, 32%) as a cream solid.NMR delta 8.78 (IH, d, J 1.5), 8.58 (IH, dd, J 1.5, 2.5), 8.54 (IH, d, J2.5), 8.30 (IH, d, J 3.0), 8.03 (IH, dd, J3.0, 8.2), 5.49 (2H, s);MS (m/e) 250 [M+H]+, Rt 0.62 (QC Method 1)

The synthetic route of 6705-33-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ARROW THERAPEUTICS LIMITED; ASTRAZENECA UK LIMITED; BARNES, Michael, Christopher, Stratton; FLACK, Stephen, Sean; FRASER, Ian; LUMLEY, James, Andrew; PANG, Pui Shan; SPENCER, Keith, Charles; TIBERGHIEN, Nathalie, Anne, Laure; TOMKINSON, Gary, Peter; WO2011/151651; (2011); A1;,
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32974-92-8, name is 1-(3-Ethylpyrazin-2-yl)ethanone, 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. COA of Formula: C8H10N2O

General procedure: The ligands L1-L4 were synthesized by reflux method. Shown in Scheme 1, 5mM of 2-Acetyl-3-ethylpyrazine and thiosemicarbazides (L1), 5mM of 2-Acetyl-3-ethylpyrazine and 4-methylthiosemicarbazide (L2), 5mM of 2-Acetyl-3-ethylpyrazine and 4-phenylthiosemicarbazide (L3), and 5mM of 2-Acetyl-3-ethylpyrazine and 3-pyrrolethiosemicarbazide (L4) were stirred in CH3OH for 3 h at 65C. The ligands were precipitated and filtered. L1-L4 were characterized by infrared spectroscopy, electrospray ionization mass spectrometry (ESI-MS), 1H NMR, and 13C NMR (Supplementary Figs S4- S31).

The synthetic route of 32974-92-8 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Khan, Muhammad Hamid; Cai, Meiling; Li, Shanhe; Zhang, Zhenlei; Zhang, Juzheng; Wen, Xiaoan; Sun, Hongbin; Liang, Hong; Yang, Feng; European Journal of Medicinal Chemistry; vol. 182; (2019);,
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Pyrazine | C4H4N2 – PubChem

Electric Literature of 27398-39-6, 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 27398-39-6 as follows.

Intermediate Z 3-(lH-Pyrazol-l-yl)pyrazine-2-carboxylic acid Intermediate Z 3-(lH-Pyrazol-l-yl)pyrazine-2-carboxylic acid (Intermediate Z) To a suspension of sodium hydride (278 mg, 6.95 mmol, 60percent in oil) in DMF (10 mL) was added lH-pyrazole (279 mg, 4.11 mmol) at RT and the resulting mixture was stirred at room temperature for 30 mins. 3-Chloropyrazine-2-carboxylic acid (500 mg, 3.16 mmol) was added and the mixture heated to 60 ¡ãC for 2 h. After cooled to RT, water (20 mL) was added and the mixture extracted with 4.7percent MeOH in DCM (20 mL x 3). The combined organic layers were washed with brine, dried over Na2S04, filtered, and concentrated in vacuo to give the title compound. LRMS m/z (M+H) 191.0 found, 191.0 required.

According to the analysis of related databases, 27398-39-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK SHARP & DOHME CORP.; KIM, Ronald; KUDUK, Scott, D.; LIVERTON, Nigel; ZHUO, Gang; (116 pag.)WO2016/100161; (2016); A1;,
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Pyrazine | C4H4N2 – PubChem

Electric Literature of 95-89-6,Some common heterocyclic compound, 95-89-6, name is 3-Chloro-2,5-dimethylpyrazine, molecular formula is C6H7ClN2, 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 23 A solution of phenylmagnesium bromide (1M in THF, 5.6 mL, 5.6 mmol) is added to a solution of 3-chloro-2,5-dimethylpyrazine (346 mg, 2.42 mmol) and Fe(acac)3 (43 mg, 0.12 mmol) in THF (10 mL) at -30 C. After stirring for 30 min at that temperature, the reaction is quenched with brine, the aqueous layer is extracted with Et2O, the combined organic phases are dried over Na2SO4 and evaporated, and the residue is purified by flash chromatography (hexane/ethyl acetate, 10:1). After eluding a first fraction containing biphenyl (212 mg), one obtains 2,5-dimethyl-3-phenylpyrazine as a pale yellow syrup (287 mg, 64%). 1H NMR (300 MHz, CD2Cl2) delta8.31 (s, 1H), 7.55-7.59 (m, 2H), 7.43-7.51 (m, 3H), 2.55 (s, 3H), 2.54 (s, 3H). 13C NMR (75 MHz, CD2Cl2) delta152.7, 150.6, 148.4, 142.1, 139.5, 129.3, 128.7, 128.6, 22.7, 21.2.

The synthetic route of 95-89-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Furstner, Alois; Leitner, Andreas; Mendez, Maria; US2003/220498; (2003); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Related Products of 768-05-8, 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 768-05-8 as follows.

General procedure: To a solution of 5.5 mmol of substituted acid hydrazides 9a or 9b in 30 mL of ethanol, 5.5 mmol of the appropriate aryl or alkylisothiocyanate 10 (isothiocyanatomethane, isothiocyanatobenzene,1-isothiocyanato-4-methoxybenzene, 1-isothiocyanatonaphthalene,1-isothiocyanato-4-nitrobenzene) was added. The mixture was refluxed for 3 h. The solid product, obtained on cooling, was washed with distilled water and recrystallized from ethanol to obtain compounds 11a-h (Ilyinet al., 2007).

According to the analysis of related databases, 768-05-8, the application of this compound in the production field has become more and more popular.

Reference:
Article; Abu Khalaf, Reema; Abdula, Ahmed Mutanabbi; Mubarak, Mohammad S.; Taha, Mutasem O.; Medicinal Chemistry Research; vol. 24; 6; (2015); p. 2529 – 2550;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Some common heterocyclic compound, 33332-29-5, name is 2-Amino-5-chloropyrazine, molecular formula is C4H4ClN3, 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. SDS of cas: 33332-29-5

General procedure: Method B is a modification of Method A and was performed under nitrogen atmosphere andwith extended work-up. Substituted benzoyl chloride (1.5 mmol, 1.2 equiv) was placed into the askunder nitrogen, diluted with dry DCM (5 mL) and dry pyridine (400 mg, 5 mmol, 4 equiv) was added.The mixture was mixed for 5 min under nitrogen. Then, 5-chloropyrazin-2-amine (162 mg, 1.25 mmol,1 equiv) dissolved in DCM (10 mL) was added dropwise over 10 min under nitrogen ow. The askwas closed by septum and stirred for additional 6 h. After reaction, the mixture was diluted with DCMto the final volume of 40 mL and washed with water (1 30 mL), 5% (m/m) aqueous NaHCO3 solution(1 30 mL), and brine (1 30 mL). The organic layer was dried over anhydrous Na2SO4 and adsorbedon silica (4 g) by evaporating the solvents under reduced pressure. Automated flash chromatographywas run using same conditions as described in Method A. If needed, the products were recrystallizedfrom hot EtOH (crystallization initiated by cooling and dropwise addition of cold water).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 33332-29-5, its application will become more common.

Reference:
Article; Zitko, Jan; Mindlova, Al?b?ta; Vala?ek, Ond?ej; Jand’ourek, Ond?ej; Paterova, Pavla; Janou?ek, Ji?i; Kone?na, Klara; Dole?al, Martin; Molecules; vol. 23; 9; (2018);,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 113305-94-5, name is 5-Aminopyrazine-2-carbonitrile, 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 113305-94-5, Application In Synthesis of 5-Aminopyrazine-2-carbonitrile

Methyl 4-((1-(tert-butoxycarbonyl)piperidin-4-yl)methylamino)-6-chloronicotinate (0.200 g, 0.52 mmol), 4-amino-cyanopyrazine (0.094 g, 0.78 mmol), cesium carbonate (0.340 g, 1.04 mmol), Pd2(dba)3 (0.021 g, 0.02 mmol) and xantphos (0.024 g, 0.04 mmol) were mixed under an argon atmosphere before the addition of toluene (3 ml_). The reaction mixture was heated at 130C for 30 minutes by microwave irradiation. The cooled mixture was dissolved in methanol – dichloromethane (1 : 1 ). The mixture was purified by ion exchange chromatography on SCX-II acidic resin (2g) eluting with methanol, then 2M ammonia-methanol. The basic fractions were combined and evaporated. Flash column chromatography eluting with ethyl acetate – hexane (1 : 3) gave methyl 4-((1-(terf- butoxycarbonyl)piperidin-4-yl)methylamino)-6-(5-cyanopyrazin-2-ylamino)nicotinate as a yellow solid (0.090 g, 37%).1H NMR (500 MHz, CDCI3) delta 1.19-1.28 (2H, m), 1.41 (9H, s), 1.79-1.82 (2H, m), 1.91- 1.97 (1H, m), 2.70-2.80 (3H, m), 3.25 (2H, t, J = 6.3 Hz), 3.86 (3H, s), 4.12-4.14 (2H, m), 6.53 (1 H, s), 7.28 (1 H, s), 8.23 (1 H, t, J = 5.3 Hz), 8.62 (1 H, s), 8.66 (1 H, d, J = 1.2 Hz), 9.16 (1H, d, J = 1.2 Hz) 9.58(1 H, s). LCMS (3) Rt 4.37 min; m/z (ESI+) 468 (MH+).

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; CANCER RESEARCH TECHNOLOGY LIMITED; WO2009/44162; (2009); 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 19745-07-4 as follows. Recommanded Product: 19745-07-4

2.3 g of benzyl alcohol was added under ice-cooling to a mixture of 3.0 g of 2,5-dichloropyrazine, 880 mg of sodium hydride (60percent, oil) and 50 mL of NMP.The reaction mixture was warmed to room temperature and stirred at room temperature for 5 hours.Water was added to the obtained reaction mixture, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure.The obtained residue was subjected to silica gel chromatography to obtain 3.1 g of Intermediate 1 represented by the following formula.

According to the analysis of related databases, 19745-07-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SUMITOMO CHEMICAL COMPANY LIMITED; NAKAJIMA, YUJI; (211 pag.)JP2017/114883; (2017); A;,
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. 38557-72-1, name is 2-Chloro-3,5-dimethylpyrazine belongs to pyrazines compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: 2-Chloro-3,5-dimethylpyrazine

Step 3: Synthesis of 3,5-Dimethyl-2-(4-naphthalen-2-yl-phenyl)pyrazine (abbreviation: Hdm2nppr)First, into a recovery flask equipped with a reflux pipe were placed 0.55 g of 2-chloro-3,5-dimethylpyrazine, 0.96 g of 4-(2-naphthyl)phenylboronic acid, 0.41 g of sodium carbonate, 0.018 g of bis(triphenylphosphine)palladium(II)dichloride (abbreviation: Pd(PPh3)2Cl2), 10 mL of water, and 10 mL of acetonitrile, and the air in the flask was replaced with argon. This reaction container was irradiated with microwaves (2.45 GHz, 100 W) for 50 minutes, so that heating was performed. Then, the reaction container was cooled to 50 C. or less. Water was added to the reaction solution, and the organic layer was extracted with dichloromethane. The obtained organic layer was washed with water and dried with magnesium sulfate. The solution which had been dried was filtered. The solvent of this solution was distilled, and recrystallized using methanol, whereby Hdm2nppr, which is the pyrazine derivative to be produced, was obtained (as a white powder in 85% yield). Note that the microwave irradiation was performed using a microwave synthesis system (Discover, manufactured by CEM Corporation). The synthesis scheme of Step 3 is illustrated in the following (c-2).

The synthetic route of 38557-72-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Semiconductor Energy Laboratory Co., Ltd.; US2011/245495; (2011); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem