Pyrazines

Adding a certain compound to certain chemical reactions, such as: 76537-18-3, name is 3-Bromo-5-chloropyrazin-2-amine, 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 76537-18-3, name: 3-Bromo-5-chloropyrazin-2-amine

A flask was charged with 3-bromo-5-chloropyrazin-2-amine (0.24 g, 1.2 mmol, D-L Chiral Chemicals), 3-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (0.24 g, 1.2 mmol, Aldrich), bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II) (0.041 g, 0.058 mmol), and cesium fluoride (0.53 g, 3.5 mmol). tert-Butyl alcohol (6.1 mL) and water (1.6 mL) were added, and the mixture was degassed and heated to 60 C. for 1.5 hours, then at 70 C. overnight, then at 100 C. for 1.5 hours. Upon cooling, the reaction mixture was partitioned between water and EtOAc, and the layers were separated. The aqueous layer was extracted with two additional portions of EtOAc and the combined organic layers were washed with brine, dried over MgSO4, filtered, and concentrated. The product was purified by flash chromatography, eluting with a gradient of 0-10% MeOH in DCM to afford a pale yellow solid (0.14 g, 58%). LCMS for C8H9ClN5 (M+H)+: calculated m/z=210.1; found 210.1.

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, 3-Bromo-5-chloropyrazin-2-amine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Incyte Corporation; Shepard, Stacey; Combs, Andrew P.; Falahatpisheh, Nikoo; Shao, Lixin; (96 pag.)US2019/276435; (2019); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Related Products of 24241-18-7, These common heterocyclic compound, 24241-18-7, name is 2-Amino-3,5-dibromopyrazine, 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.

[0953] To a solution of3,5-dibromopyrazin-2-amine (234g, 932 mmol) in DCM (700 mL) and titanium (IV) chloride(174 g, 926 mmol), tert-butyl nitrite (572 g, 5.55 mol) wasslowly added. The resulting mixture was stirred for 2 h atroom temperature and treated with water (500 mL). Theresulting mixture was extracted with DCM (3×500 mL). Thecombined organic layers were concentrated under reducedpressure. The resultant residue was purified by flash colunmchromatography on silica gel (EtOAc/petroleum ether (1:50v/v)) to obtain compound 90d as colorless oil (210 g, 83%yield). Mass Spectrum (LCMS, ESI pos.): Calcd. forC4 HBr2ClN2 : 272.8 (M+H). found 272.6.

The synthetic route of 24241-18-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JANSSEN PHARMACEUTICA, NV; Player, Mark R.; Meegalla, Sanath K.; Illig, Carl R.; Chen, Jinsheng; Wilson, Kenneth J.; Lee, Yu-Kai; Parks, Daniel J.; Huang, Hui; Patel, Sharmila; Lu, Tianbao; US2014/364414; (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 951626-95-2 as follows. Product Details of 951626-95-2

A solution of lithium hydroxide monohydrate (2.73 g, 65.0 mmol) in H20 (30.0 mL) was added to a suspension of ethyl 4-oxo-4,5 ,6,7-tetrahydropyrazolo [1,5 -a]pyrazine-2- carboxylate (2.72 g, 13.0 mmol) in THF (30 mL) and MeOH (30 mL) at 0 C. Then, the suspension was stirred at rt overnight. The solvents were removed. H20 (20 mL) wasadded. The clear solution was cooled to 0 C, conc. HC1 (5.42 mL, 65.0 mmol) was added to bring pH to 3. The suspension was stirred at 0 C for 2 h, filtered, and dried to give a white solid (2.2 g, 93%). LC-MS(ESI) m/z: 182.1 [M+H].

According to the analysis of related databases, 951626-95-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; LADZIATA, Vladimir; GLUNZ, Peter W.; HU, Zilun; WANG, Yufeng; (0 pag.)WO2016/10950; (2016); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 1379338-74-5,Some common heterocyclic compound, 1379338-74-5, name is 5,7-Dichloropyrido[3,4-b]pyrazine, molecular formula is C7H3Cl2N3, 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.

Intermediate 22: 1 ,1-Dimethylethyl (2/~)-2-{r(7-chloropyridor3,4-6lpyrazin-5- yl)amino1methylV4-morpholinecarboxylate; 1 , 1-dimethylethyl (2f~)-2-(aminomethyl)-4-morpholinecarboxylate (for preparation see: J. Medicinal Chemistry, 2009, 52 (15), 4810-4819) (6g, 27.7mmol) was dissolved in N-methyl-2-pyrrolidinone (NMP) (60ml_) and to this was added DIPEA (7.27ml_, 41.6mmol) and 5,7-dichloropyrido[3,4-b]pyrazine (5.55g, 27.7mmol). This was split between 4 large microwave vials and each was heated at 130C for 30min. They were monitored by LCMS and were given a further 10min at 130C. The reaction mixtures were partitioned between ethyl acetate (700ml) and diluted aqueous ammonium chloride (1 litre). The aqueous was reextracted with ethyl acetate (300ml) and the combined organics were washed with aqueous ammonium chloride (500ml), dried over sodium sulfate and concentrated in vacuo to yield a crude brown oil. It was dissolved in DCM and passed through silica (70g) eluting with DCM (6 X 40ml) then 5% ethyl acetate in DCM (2 X 40ml), 10% ethyl acetate in DCM (5 X 40ml) then 15% ethyl acetate in DCM (2 X 40ml) then 20%ethyl acetate in DCM (2 X 40ml). Appropriate fractions were combined and concentrated in vacuo to yield: N8231-100-2, orange-yellow slightly gummy solid, 7.7gLCMS (Method B): Rt = 1.17min, MH+ 380

The synthetic route of 1379338-74-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXO GROUP LIMITED; ATKINSON, Francis Louis; ATKINSON, Stephen John; BARKER, Michael David; DOUAULT, Clement; GARTON, Neil Stuart; LIDDLE, John; PATEL, Vipulkumar Kantibhai; PRESTON, Alexander G; SHIPLEY, Tracy Jane; WILSON, David Matthew; WATSON, Robert J; WO2012/123312; (2012); 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. 313339-92-3, name is 3,5-Dichloropyrazine-2-carbonitrile, A new synthetic method of this compound is introduced below., HPLC of Formula: C5HCl2N3

A nilxture of 3,5-dichloropyrazine-2-carbonitrile (150 mg, 0.87 mmol), 1- methyl-4-(4,4,5 ,5 -tetramethyl- 1,3 ,2-dioxaborolan-2-yl)- 1H-pyrazole (180 mg 0.87 mmol, 1.0 equiv), [1,1 ?-bis(diphenylphosphino)ferroceneldichloropalladium(II) (0.04 mmol, 5 mol%) in degassed THF (1.7 mL) and aq. solution of sodium carbonate (2 M, 850 jiL) was stirred for 4h under nitrogen at 100C. Once complete, the reaction was diluted with EtOAc and water. The organic phase was separated and the aqueous layer was extracted twice with EtOAc, dried over magnesium sulfate, filtered and concentrated under reduced pressure to give product: ESI-MS (mlz): 220.1

The synthetic route of 313339-92-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CASE WESTERN RESERVE UNIVERSITY; BOARD OF REGENTS, THE UNIVERSITY OF TEXAS SYSTEM; MARKOWITZ, Sanford; ANTCZAK, Monika; READY, Joseph; ZHANG, Youngyou; (332 pag.)WO2018/218251; (2018); 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. 16298-03-6, name is Methyl 2-aminopyrazine-3-carboxylate, A new synthetic method of this compound is introduced below., HPLC of Formula: C6H7N3O2

A solution of methyl 3-aminopyrazine-2-carboxylate (3.0 g, 19.6 mmol) and NBS(3.5 g, 23.5 mol) in MeCN (70 mL) was stirred at 70C for 5 h. Then the mixture was concentrated and extracted with EtOAc. The organic layer was washed with Na2503 (a.q.) and brine, dried over Na2504 and concentrated in vacuo. The crude product of methyl 3-amino-6-bromopyrazine-2-carboxylate (3.0 g, yield: 92%) was used for next step without further purification. ?H-NMR(CDC13, 400 MHz) 8.18 (s, 1H), 6.546.93 (m, 2H), 3.86 (s, 3H). MS (M+H): 232 / 234.

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.; DAI, Xing; LIU, Hong; PALANI, Anandan; HE, Shuwen; NARGUND, Ravi; XIAO, Dong; ZORN, Nicolas; DANG, Qun; MCCOMAS, Casey C.; PENG, Xuanjia; LI, Peng; SOLL, Richard; WO2014/205593; (2014); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 5049-61-6,Some common heterocyclic compound, 5049-61-6, name is Pyrazin-2-amine, molecular formula is C4H5N3, 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.

Aminopyrazine (95g, 1 mol) in chloroform (2.5 L) was cooled to between O0C and -5C. N-bromosuccimide (375 g, 2.1 mol) was then added over a 6 hour period, during which time the temperature was kept below O0C. The reaction mixture was stored in a freezer overnight and then stirred vigorously and quenched with water (1 L). The mixture was filtered through glass wool and the phases separated. The organic phase was washed with 10% K2CO3 (aq, 1 L), dried over MgSO4, and concentrated in vacuo. The residue was triturated with hexane and ethyl acetate. The yellow/brown solid was filtered and dried under high vacuum in a desiccator overnight to give the title compound (119 g). 1H (270MHz, CDCI3) 4.99 (2H, bs), 8.09(1H, s); LC-MS (AP+): 254:256 (1:1 isotopes, M+H+).

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

Reference:
Patent; CANCER RESEARCH TECHNOLOGY LIMITED; WO2008/74997; (2008); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 186534-02-1, The chemical industry reduces the impact on the environment during synthesis 186534-02-1, name is 3,5,6-Trimethylpyrazine-2-carbaldehyde, I believe this compound will play a more active role in future production and life.

General procedure: To a stirred solution of 4-1 (0.25 mmol) in CH3OH (1.5 mL) andTHF (1.5 mL) was added compounds 5a-q (0.28 mmol) at room temperature.Keep stirring for 2-9 h to give intermediate 6a-q which wasdirectly cooled to 0 C without any treatment. Then the mixture wasadded to NaBH4 (1.25 mmol), keeping stirring for 2 h. The reaction wasquenched with 10% HCl aqueous and directly evaporated to dryness.The residue was basified with saturated NaHCO3 solution and extractedwith DCM (3 × 10 mL). Subsequently, the combined organic layerswere washed with brine (20 mL), dried over Na2SO4, filtered, concentratedand purified via column chromatograph (eluting solvent:pentane/ethyl acetate=10/1 to 4/1) to afford the desired products 7aq.Meanwhile, product 7r was obtained from compound 4-2 andcompound 5i by the same synthesis method. The yield is 47-76%.

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, 3,5,6-Trimethylpyrazine-2-carbaldehyde, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Cao, Zhongcheng; Deng, Yong; Liu, Zhuoling; Song, Qing; Tan, Zhenghuai; Yang, Ziyi; Yu, Guangjun; Bioorganic and medicinal chemistry; (2020);,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application of 109838-85-9,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.

Example 1; (2S)-2- (fert-butoxycarbonyl) aminol-3-cLrcloheptylpropanoic acid building block; a) Methyl (2S)-2-amino-3-cycloheptylpropanoate; To a stirred solution of R-2,5-dihydro-3, 6-dimethoxy-2-isopropyl pyrazine (5 g, 27 mmol) in THF (80 mL) at-78 °C was added dropwise 2.5 M n-butyllithium in hexanes over 40 min, maintaining the temperature of the reaction mixture below-70 °C. To the reaction mixture was added dropwise a solution of iodomethylcycloheptane (Webb et al, J. Med. Chem. , 42,8 (1999), 1415-1421. ) (6.8 g, 28. 5 mmol) in THF (12 mL) over 50 min, maintaining the temperature of the reaction mixture below-70 °C. The reaction mixture was then stirred at 0 °C for another 75 min, acetic acid was added (2.45 mL) and stirring was continued for another 20 min. The reaction mixture was then diluted with ethyl acetate (200 mLI), washed with brine (2 x 50 mLI), dried (MgS04), filtered and concentrated in vacuo. Column chromatography of the residue using stepwise gradient elution (ethyl acetate in hexane 0-5percent) gave the pyrazine derivative as an oil (5.4 g, 68percent). A mixture of the pyrazine derivative (5.4 g, 18.5 mmol) in acetonitrile (55 mL), water (45 mL) and 1 M aqueous hydrochloric acid (45 mL) was stirred at room temperature for 2 h, then concentrated in vacuo to approximately half the volume. Aqueous NaHCO3 (1 M) was added until just alkaline, then the reaction was extracted with dichloromethane (3 x 50 mL). The extracts were dried (MgSO4), filtered and concentrated in vacuo onto silica. Column chromatography of the residue using stepwise gradient elution (ethyl acetate in hexane and triethylamine (0.5percent) 20-100percent) gave pure fractions of (8) which were concentrated in vacuo to a syrup (2.14 g, 58percent). Additional material could be obtained by repeated chromatography.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route (R)-2-Isopropyl-3,6-dimethoxy-2,5-dihydropyrazine, its application will become more common.

Reference:
Patent; MEDIVIR UK LTD; PEPTIMMUNE, INC; WO2005/82876; (2005); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 1458-18-0, The chemical industry reduces the impact on the environment during synthesis 1458-18-0, name is Methyl 3-amino-5,6-dichloropyrazine-2-carboxylate, I believe this compound will play a more active role in future production and life.

Production Example 18-1 Methyl 3-amino-5,6-dimethylpyrazine-2-carboxylate A mixture of methyl 3-amino-5,6-dichloro-2-pyrazine carboxylate (200 mg, 0.90 mmol), X-Phos (170 mg, 0.36 mmol), tris(dibenzylideneacetone)dipalladium(0) (82 mg, 0.090 mmol), tetramethyltin (0.31 mL, 2.3 mmol), and N-methylpyrrolidinone (2 mL) was stirred at 130 C. for 2 hours under microwave irradiation. The reaction mixture was cooled to room temperature, water was added thereto at the same temperature, and the resulting mixture was extracted with ethyl acetate. The organic layer was washed with a saturated saline solution, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate_heptane=3:2) to obtain the title compound (80 mg, 49% yield). 1H-NMR Spectrum (400 MHz, CDCl3) delta (ppm): 2.44 (s, 3H), 2.46 (s, 3H), 3.97 (s, 3H), 6.22 (br s, 2H).

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, Methyl 3-amino-5,6-dichloropyrazine-2-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Eisai R&D Management Co., Lt.d; Tanaka, Keigo; Fukuyama, Takashi; Murai, Norio; Itano, Wataru; Hirota, Shinsuke; Iida, Daisuke; Azuma, Hiroshi; (32 pag.)US2016/168176; (2016); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem