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. 100047-56-1, name is 5-Bromo-3-methylpyrazin-2-ol, A new synthetic method of this compound is introduced below., Formula: C5H5BrN2O

(ls,4s)-4-(l-Methylpiperidin-4-yloxy)cyclohexanol (1.2 g, 5.63 mmol) was dissolved inTHF (10 mL), 5-bromo-3-methylpyrazin-2-ol (1.170 g, 6.19 mmol) and triphenylphosphine (1.771 g, 6.75 mmol) were added, then cooled down in an ice -water bath. DIAD (1.329 ml, 6.75 mmol) was added dropwise under N2. The reaction mixture was slowly warmed to room temperature, stirred overnight, and concentrated. The residue was purified by preparative HPLC (15-80% CH3CN/H20 with 0.1 % TFA over 30 min) and column chromatography (5% methanol/ethyl acetate containing 1 % Et3N) to give the title compound (525 mg, 1.366 mmol, 24.3% yield). Exact mass calculated for Ci7H26BrN302: 383.1 , found: LCMS m/z = 384.2[M+H]+; lU NMR (400 MHz, CDC13) 5 ppm 1.45-1.62 (m, 4H), 1.65-1.75 (m, 2H), 1.91-2.05 (m, 4H), 2.05-2.15 (m, 2H), 2.39 (s, 3H), 2.36-2.42 (m, 2H), 2.42 (d, J = 0.7 Hz, 3H), 2.78-2.85 (m, 2H), 3.46-3.54 (m, 2H), 4.95-5.02 (m, 1H), 7.98 (d, J = 0.6 Hz, 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

Electric Literature of 33332-30-8, 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 33332-30-8 as follows.

Example 90 2-Methoxy-6-(‘4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl’)pyrazine-; A mixture of 2-chloro-6-methoxypyrazine (0.50 g, 3.46 mmol), bis(pinacolato)diboron (0.966 g, 3.80 mmol), tris(dibenzylideneacetone)dipalladium(0) (0.095 g, 0.10 mmol), tricyclohexyl phosphine (0.116 g, 0.42 mmol) and potassium acetate (0.509 g, 5.19 mmol) in 1,2-dimethoxy ethane (10 mL) was run for 3h at 15O0C in a microwave oven under argon atmosphere. The reaction mixture was partitioned between water and diethyl ether and the organic phases were pooled, dried over magnesium sulfate, filtered and concentrated to give 1.15 g (quantative yield) of the crude title compound which was used in the next reaction step without further purification; MS (CI) m/z 237.

According to the analysis of related databases, 33332-30-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ASTRAZENECA AB; ASTEX THERAPEUTICS LTD; WO2007/145571; (2007); 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. 2847-30-5, name is 2-Methoxy-3-methylpyrazine, A new synthetic method of this compound is introduced below., HPLC of Formula: C6H8N2O

2-Methoxy-3-methylpyrazine 1a (3.72 g, 30 mmol) was added slowly to a stirred mixture of HNO3 (5.5 ml, 100%) and H2SO4 (11 ml, 98%) at 30-35 C. The reaction mixture was heated at 45 C for 4 h. Afterwards, it was poured over ca. 50 g of crushed ice and extracted with EtOAc (3¡Á50 ml). Combining the organic layers, washing with brine, drying (MgSO4), and removal ofsolvent afforded a mixture of products.The residue was subjected to column chromatography [eluting with hexane-EtOAc, 50:1? 5:1, Rf(2a) > Rf(3a) > Rf(4a) > Rf(5a)] to give pure products.

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; Yudin, Igor L.; Palysaeva, Nadezhda V.; Averkiev, Boris B.; Sheremetev, Aleksei B.; Mendeleev Communications; vol. 25; 3; (2015); p. 193 – 195;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Related Products of 74290-68-9, 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. 74290-68-9, name is 6-Bromo-5-methylpyrazin-2-amine belongs to pyrazines compound, it is a common compound, a new synthetic route is introduced below.

6-Bromo-5-methylpyrazin-2-amine (which may be prepared according to the method ofN. Sato, J. Heterocycl. Chem. 1980, 171, 143-147) (2.40 g, 12.8 mmol), 4-[3-methyl-4-(4,4,5,5- tetramethyl- 1,3 ,2-d ioxaborolan-2-yl)phenoxy]furo[3,2-c]pyridine (C2) (4.48 g, 12.8 m mol), and tetrakis(triphenylphosphine)palladium(0) (95%, 466 mg, 0.383 mmol) were combined in a pressure tube and dissolved in 1 ,4-dioxane (60 mL) and ethanol (20 mL). A solution of sodium carbonate (2.0 M in water, 19.1 mL, 38.2 mmol) was added, and argon was bubbled through thereaction mixture for 15 minutes. The tube was sealed, and then heated at 140 00 for 16 hours. The reaction mixture was combined with a second, identical, reaction mixture for workup. The combined reaction mixtures were filtered; solids remaining in the reaction vessels were slurried in water and filtered, and the filter cake was washed with ethanol. All of the organic filtrates were passed through a pad of Celite, and the Celite pad was washed with ethanol. These filtrates were concentrated in vacuo, and the resulting solid was slurried in water, filtered and washedwith water. The solid was then slurried in 1:1 heptane I diethyl ether, filtered and washed withdiethyl ether to afford the product as a light yellow solid. Yield: 6.774 g, 20.38 mmol, 80%. 1HNMR (500 MHz, DMSO-d6) oe 8.14 (d, J=2.2 Hz, 1H), 8.01 (d, J=5.7 Hz, 1H), 7.82 (s, 1H), 7.47(dd, J=5.8, 0.9 Hz, 1H), 7.21 (d, J=8.3 Hz, 1H), 7.15 (brd, J=2.4 Hz, 1H), 7.09 (brdd, J=8.2, 2.4Hz, 1H), 7.06 (dd, J=2.2, 0.7 Hz, 1H), 6.18 (br s, 2H), 2.12 (s, 3H), 2.07 (br s, 3H).

The synthetic route of 6-Bromo-5-methylpyrazin-2-amine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PFIZER INC.; COE, Jotham, Wadsworth; ALLEN, John, Arthur; DAVOREN, Jennifer, Elizabeth; DOUNAY, Amy, Beth; EFREMOV, Ivan, Viktorovich; GRAY, David, Lawrence, Firman; GUILMETTE, Edward, Raymond; HARRIS, Anthony, Richard; HELAL, Christopher, John; HENDERSON, Jaclyn, Louise; MENTE, Scot, Richard; NASON, Deane, Milford, II; O’NEIL, Steven, Victor; SUBRAMANYAM, Chakrapani; XU, Wenjian; WO2014/72881; (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 5521-61-9 as follows. name: 6-Methylpyrazine-2-carboxylic acid

INTERMEDIATE 71 PREPARATION OF (6-METHYLPYRAZIN-2-YL)METHANOL To a solution of 6-methylpyrazine-2-carboxylic acid (8.00 g, 58.0 mmol) in N,N- dimethylformamide (50 mL) were added Cs2CO3 (37.8 g, 116 mmol) and iodomethane (12.3 g, 87.0 mmol). After being stirred overnight at room temperature, the reaction mixture was quenched with water (100 mL) and extracted with EtOAc (5 x 150 mL). The combined organic layers were washed with brine (100 mL), dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was then diluted with water (50 mL). NaBH4 (12.5 g, 330 mmol) was added portionwise at 0 C. After addition, the resulting mixture was stirred at room temperature for 30 min, cooled to 0 C, diluted with water (150 mL) and extracted with EtOAc (8 x 100 mL). The combined organic layers were washed with brine (200 mL), dried over Na2SO4, filtered and concentrated under reduced pressure to afford the title compound (2.9 g, crude) as a yellow solid.1H NMR (400 MHz, DMSO-d6) delta 8.50 (s, 1H), 8.42 (s, 1H), 5.55 (t, J = 5.8 Hz, 1H), 4.59 (d, J = 5.5 Hz, 2H), 2.47 (s, 3H).

According to the analysis of related databases, 5521-61-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; DENALI THERAPEUTICS INC.; BONANOMI, Giorgio; ESTRADA, Anthony A.; FENG, Jianwen A.; FOX, Brian; LESLIE, Colin Philip; LYSSIKATOS, Joseph P.; NAPOLITANO, Carmela; POZZAN, Alfonso; SUDHAKAR, Anantha; SWEENEY, Zachary K.; TONELLI, Federica; DE VICENTE FIDALGO, Javier; (232 pag.)WO2017/96301; (2017); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Some common heterocyclic compound, 5910-89-4, name is 2,3-Dimethylpyrazine, molecular formula is C6H8N2, 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 2,3-Dimethylpyrazine

A mixture of 2,3-dimethylpyrazine (2Og, 18.5mmol), selenium dioxide (41.06g, 37mmol) and diatomeous earth (2Og) in EtOAc (500ml) was stirred and heated at 7O0C for 2 hours. The mixture was allowed to cool and the insoluble matter was removed by filtration EPO through diatomeous earth. The filtrate was washed with saturated aqueous sodium hydrogen carbonate solution and then saturated aqueous sodium chloride solution, dried (MgSO4) and the solvent removed by evaporation. The residue was suspended in water (100ml) and hydroxylamine (45ml of a 50% aqueous solution) was added. The mixture was stirred at ambient temperature for 18 hours and the mixture then extracted with EtOAc. The extracts were combined, washed with saturated aqueous sodium chloride solution, dried (MgSO4) and the solvent removed by evaporation. The residue was triturated with isohexane to give 3- methylpyrazine-2-carboxaldehyde oxime (9.65g, 38%); NMR Spectrum 2.67 (s, 3H), 8.23 (s, IH), 8.45-8.49 (m, 2H), 11.87 (s, IH).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5910-89-4, its application will become more common.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2006/106307; (2006); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 127406-08-0, name is 4-(Pyrazin-2-yl)benzaldehyde, 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 127406-08-0, Computed Properties of C11H8N2O

General procedure: A mixture of HPLC-purified aminooxy-His containing peptide (30 mM in DMSO, 10 muL), aldehyde (30 mM in DMSO, 10 muL) and acetic acid (150 mM in DMSO, 10 muL) was agitated at room temperature (overnight). Crude reaction mixtures were used directly for Plk1 PBD binding ELISA assays. Structures of oxime-containing peptides are shown in Table S1.

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, 4-(Pyrazin-2-yl)benzaldehyde, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Zhao, Xue Zhi; Hymel, David; Burke, Terrence R.; Bioorganic and Medicinal Chemistry Letters; vol. 26; 20; (2016); p. 5009 – 5012;,
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 25513-92-2 as follows. Application In Synthesis of Ethyl 3-methylpyrazine-2-carboxylate

Example 1.3: Preparation of 3-bromomethyl-pyrazine-2-carboxylic acid ethyl esterA mixture of 3-methyl-pyrazine-2-carboxylic acid ethyl ester (Example 1.1) (0.5 g), N-bromosuccinimide (“NuBS”) (0.536 g) and 2,2′-azobis(2-methylpropionitrile) (“AIBNu”) (0.487 g) in carbon tetrachloride (2.5 ml) was heated to reflux. After 1 hour thin layer chromatography showed a mixture of starting material and the desired product. Further NuBS (0.536 g) and AIBNu (0.243 g) were added and the reaction mixture heated for a further 1 hour. The percentage of product increased and impurities began to form. The reaction mixture was cooled to ambient temperature and then to 0C. The cold mixture was filtered and the filtrate concentrated. The residue was purified by chromatography on silica gel(eluent: 0-10% v/v ethyl acetate in zso-hexane) to give 3-bromomethyl-pyrazine-2-carboxylic acid ethyl ester (640 mg) contaminated with 3-methyl-pyrazine-2-carboxylic acid ethyl ester (due to co-elution, -3:2). MH+ – 245, RT = 1.26 min (Method A).

According to the analysis of related databases, 25513-92-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SYNGENTA LIMITED; WILLETTS, Nigel, James; MULHOLLAND, Nicholas, Phillip; WORTHINGTON, Paul, Anthony; AVERY, Alaric, James; WO2010/130970; (2010); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Some common heterocyclic compound, 5910-89-4, name is 2,3-Dimethylpyrazine, molecular formula is C6H8N2, 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. HPLC of Formula: C6H8N2

(a) A solution of 10.0 g (93.0 mmol) 2,3-dimethylpyrazine and70.0 g (390 mmol) N-bromo-succinimide in 800 ml CCl4 was irradiatedwith a 250 Watt lamp at reflux temperature during 20 h. After cooling the solution was filtered and the organic phase waswashed with a 5% sodium thiosulfate solution and water. Afterevaporation of the organic phase, the residue was crystallized inethanol to give 29.1 g 2,3-bis-dibromomethyl-pyrazine (25) (74%).1H NMR (CDCl3, 400 MHz): 7.1 (s, 2H), 8.6 (s, 2H). MS (electrospray):m/z = 420 [M+1], 422 [M+3], 424 [M+5], 426 [M+7], 428 [M+9]. Mp: 167-170 C.(b) To a solution of 38.0 g (90.0 mmol) 2,3-bis-dibromomethylpyrazine(25) and 70.0 g (400 mmol) diethyl maleate in 450 mlDMF was added 40.0 g (270.0 mmol) NaI and the mixture washeated at 80 C during 20 h. After evaporation of the solvent, theresidue was dissolved in 1000 ml t-butyl-methyl ether and washedwith a 5% sodium thiosulfate solution and water (5 times). Evaporationof the solvent and purification of the residue with flashchromatographygave 9.1 g quinoxaline-6,7-dicarboxylic aciddiethyl ester (26) (37%) as a dark oil.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5910-89-4, its application will become more common.

Reference:
Article; Jeanguenat, Andre; Durieux, Patricia; Edmunds, Andrew J.F.; Hall, Roger G.; Hughes, Dave; Loiseleur, Olivier; Pabba, Jagadish; Stoller, Andre; Trah, Stephan; Wenger, Jean; Dutton, Anna; Crossthwaite, Andrew; Bioorganic and Medicinal Chemistry; vol. 24; 3; (2016); p. 403 – 427;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

These common heterocyclic compound, 5521-61-9, name is 6-Methylpyrazine-2-carboxylic acid, 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. Quality Control of 6-Methylpyrazine-2-carboxylic acid

Step 5: 5-|(6-Meth l-p razine-2-carbonyl)-amino|-bicyclo|3.2.1joctane-l-carboxylic acid ethyl ester5-Amino-bicyclo[3.2.1 ]octane- l -carboxylic acid ethyl ester (0.5 g, 2.53 mmol) was dissolved in methylene chloride (10.0 mL, 156 mmol). 6-Methylpyrazine-2-carboxylic acid (0.35 g, 2.53 mmol), benzotriazol- 1 -yloxytris(dimethylamino)phosphonium hexafluorophosphate ( .12 g, 2.53 mmol) and triethylamine (0.71 mL. 5.07 mmol) in methylene chloride (10.0 mL, 156 mmol) were added. The mixture was stirred at rt for 2 hours. The mixture was concentrated under reduced pressure. The resulting residue was purified on the Co b FI sh J system (hexane/ethyl acetate: 100/0 to 30/70 in 8 min, then hexane/ethyl acetate: 30/70) to afford 0.60 g (75percent) of the desired product. ESI-MS m/z: 3 18 (M + H)+

The synthetic route of 6-Methylpyrazine-2-carboxylic acid has been constantly updated, and we look forward to future research findings.

Reference:
Patent; H. LUNDBECK A/S; LI, Guiying; ZHOU, Hao; WEISS, Jesse; DOLLER, Dario; FORD, James; WO2012/88365; (2012); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem