Month: August 2021

Synthetic Route of 89180-45-0,Some common heterocyclic compound, 89180-45-0, name is 5-Chloro-2-hydroxypyrazine, molecular formula is C4H3ClN2O, 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 50 mL round bottom flask equipped with a stir bar was added 5- chloropyrazin-2-ol (250 mg, 1.9 15 mmol), 2-(4-fluorophenyl)ethanol (268 mg, 1.9 15 mmol), triphenylphosphine (603 mg, 2.298 mmol) and THF (10 mL). To the stirred solution was added DIAD (0.447 mL, 2.298 mmol). The solution had a mild exotherm, then cooled within 5 minutes. The solution was stirred at RT for 2 hrs. The reactionsolution was concentrated in vacuo and the resulting oil was purified via silica gel chromatography (40 g column, 5-40% EtOAc:Hex) to afford the product 2-chloro-5-(4-fluorophenethoxy)pyrazine (330 mg, 1.306 mmol, 68.2 % yield) as a white solid. ?H NMR (500 MHz, CDC13) 8.10 (d,J=1.3 Hz, 1H), 8.01 (d,J=1.3 Hz, 1H), 7.25 (dd, J=8.6, 5.4 Hz, 2H), 7.03 (t, J=8.7 Hz, 2H), 4.52 (t, J=6.9 Hz, 2H), 3.09 (t, J=6.9 Hz, 2H). LCMS (M+1) = 253.0.

The synthetic route of 89180-45-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; VIIV HEALTHCARE UK (NO.5) LIMITED; BELEMA, Makonen; BOWSHER, Michael S.; DESKUS, Jeffrey A; EASTMAN, Kyle J.; GILLIS, Eric P; FRENNESSON, David B; IWUAGWU, Christiana; KADOW, John F.; NAIDU, B. Narasimhulu; PARCELLA, Kyle E.; PEESE, Kevin M; SAULNIER, Mark G; SIVAPRAKASAM, Prasanna; (463 pag.)WO2018/127800; (2018); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 19745-07-4,Some common heterocyclic compound, 19745-07-4, name is 2,5-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.

Preparation of 4-benzyl- 1 -(5-chloropyrazin-2-yl)piperidin-4-amine. To a solution of 2,5-dichloropyrazine (0.1316 mL, 0.7243 mmol) in DMSO (10 mL) were added K2CO3 (300.3 mg, 2.173 mmol) followed by 4-benzylpiperidin-4-amine bis(2,2,2- trifluoroacetate) (303 mg, 0.72 mmol). The reaction was sealed and heated at 75 °C overnight. After cooling to RT, the reaction was diluted with EtOAc (10 mL) and water (20 mL). After phase-separation, the aqueous was extracted with EtOAc (2x). The combined organic extracts were concentrated and used directly in the next step. MS (apci) m/z = 303.1 (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 2,5-Dichloropyrazine, its application will become more common.

Reference:
Patent; ANDREWS, Steven W.; ARONOW, Sean; BLAKE, James F.; BRANDHUBER, Barbara J.; COLLIER, James; COOK, Adam; HAAS, Julia; JIANG, Yutong; KOLAKOWSKI, Gabrielle R.; MCFADDIN, Elizabeth A.; MCKENNEY, Megan L.; MCNULTY, Oren T.; METCALF, Andrew T.; MORENO, David A.; RAMANN, Ginelle A.; TANG, Tony P.; REN, Li; WALLS, Shane M.; (946 pag.)WO2018/71454; (2018); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application of 33332-29-5, 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. 33332-29-5, name is 2-Amino-5-chloropyrazine belongs to pyrazines compound, it is a common compound, a new synthetic route is introduced below.

Step A: 2-Chloro-5-isothiocyanatopyrazine CINSA solution of 5-chloropyrazin-2-amine (13.0 g, 100 mmol) and 1,1?- thiocarbonyldipyridin-2(1H)-one (27.9 g, 120 mmol) was stirred in DCM (200 mL)at room temperature for 1 h. The reaction was concentrated to ca. 100 mL volume and filtered through a pad of silica gel (1 L), washing with ethyl acetate in hexanes (10%). The filtrate was concentrated and dried to afford 2-chloro-5- isothiocyanatopyrazine (14.3 g, 83.0 mmol, 83 % yield). ?H NMR (400 MHz, chloroform-cl) 5 ppm 8.38 (d, J=1.26 Hz, 1 H) 8.18 (d, 1=1.26 Hz, 1 H). MS(LC/MS) R.T. = 1.84; [M+H] = 172.09.

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, 2-Amino-5-chloropyrazine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; HILL, Matthew D.; FANG, Haiquan; WO2013/177024; (2013); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 4774-14-5, name is 2,6-Dichloropyrazine, 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 4774-14-5, HPLC of Formula: C4H2Cl2N2

To a -20 C. solution of n-butyllithium (2.5 M in hexane, Aldrich, 26.5 mmol) in dry tetrahydrofuran (200 mL) under argon was added 2,2,6,6-tetramethylpiperidine (Aldrich, 11.5 mL, 66.5 mmol, 1.22 eq). The resulting solution was warmed to 0 C. over 0.5 hour period. The solution was then cooled to -78 C., and a solution of 2,6-dichloropyrazine (Aldrich, 8.24 g, 55.3 mmol, 1.0 eq) in tetrahydrofuran was slowly added via a syringe. After addition was complete, the resulting mixture was stirred at -78 C. for an additional 1 hour after which 2-chlorobenzaldehyde (Aldrich, 9.3 mL, 83 mmole, 1.5 eq) was added drop wise via a syringe. The reaction mixture was stirred for an additional 1 hour, quenched with hydrochloric acid (18 mL, 220 mmol, 4 eq)/ethanol (75 mL)/tetrahydrofuran (90 mL) mixture, and then warmed to room temperature. The reaction mixture was diluted with aqueous saturated sodium bicarbonate solution and extracted with ether. The organic layer was separated and washed with brine, dried over sodium sulfate, filtered, and concentrated to give a crude oil which was purified via chromatography using dichloromethane/hexanes (1:1) as the eluent to give (2-chlorophenyl)-(3,5-dichloropyrazin-2-yl)methanol (12.8 g, 44 mmol, 80% yield). Mass spec, M+1=290.

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; Roche Palo Alto LLC; US2005/203091; (2005); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 110223-15-9, name is 2-Amino-3-benzyloxypyrazine, 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 110223-15-9, Computed Properties of C11H11N3O

2-Bromo-4,4, 4-trifluoro-3-oxo-butyric acid ethyl ester (2.61 g, 9.9 mmol) was added to a solution of 2-amino-3-benzyloxypyrazine (Compound m in Scheme 1, 1 g, 5.0 mmol) in ethanol (10 mL). The reaction mixture was refluxed for 5 h. Upon cooling, a yellow precipitate formed from the reaction mixture. The solid was collected and washed with ice-cold ethanol to give a light yellow solid (0. 82g, 61%). 1H-NMR (CD3OD-d4) No. 8. 23 (d, J5. 9 Hz, 1H), 7.10 (d, J5. 9 Hz, 1H), 4.47 (q, J 7.1 Hz, 2H), 1.41 (t, J7. 1 Hz, 3H); MS (ES1) 276.0 ([M+H] +).

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; CARDIOME PHARMA CORPORATION; WO2005/34837; (2005); A2;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 870787-06-7,Some common heterocyclic compound, 870787-06-7, name is 3-(Trifluoromethyl)pyrazine-2-carboxylic acid, molecular formula is C6H3F3N2O2, 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.

General procedure: A 100 mL round bottom flask was charged with the compound represented by the formula (II-1) (2 mmol), EDCI (2.4 mmol), HOBt (2.4 mmol) and 10 mL of DMF, and reacted at 25 C. for 1 h. Then, the compound (2.4 mmol) represented by the formula (II-2) was added to the above solution and reacted at 25C for 24 hours. After the solvent was removed, the target product was obtained by column chromatography.

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

Reference:
Patent; Central China Normal University; Yang Guangfu; Li Hua; Xiong Li; (34 pag.)CN108069915; (2018); A;,
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. 91476-80-1, name is 5,6,7,8-Tetrahydroimidazo[1,2-a]pyrazine, A new synthetic method of this compound is introduced below., Product Details of 91476-80-1

A mixture of (2-chloropyrimidin-4-yl)-(l -isopropyl-1 H-imidazo[4,5-c]pyridin-6-yl)amine (Example 12, step 4) (70 mg, 0.24 mmol), 5,6,7,8-tetrahydroimidazo[l,2-a]pyrazine (44 mg, 0.36 mmol), triethylamine (0.15 mL) in isopropyl alcohol (0.5 mL) was heated at 150 C under microwave irradiation on high absorbance for 2.5 h. The cooled reaction mixture was poured onto an SCX cartridge; the cartridge was washed with MeOH followed by elution of the product with 2M NH3 in MeOH. The product containing fractions were concentrated in vacuo and the resulting residue was crystallised from MeOH/EtOAc to afford the title compound as a white solid (55 mg, 62%). LCMS (ESI): RT 1.72 min, [M+H]+ 376.0, Method = E. lH NMR (400 MHz, CDC13): delta 8.75 (1H, d, J = 1.0 Hz), 8.29 (1H, s), 8.06 (1H, d, J = 5.7 Hz), 7.95 (1H, s), 7.66 (1H, s), 7.02 (1H, d, J = 1.3 Hz), 6.86 (1H, d, J = 1.3 Hz), 6.22 (1H, d, J = 5.7 Hz), 5.08 (2H, s), 4.79-4.67 (1H, m), 4.30 (2H, t, J = 5.4 Hz), 4.07 (2H, t, J = 5.4 Hz), 1.70 (6H, d, J = 6.7 Hz).

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; GENENTECH, INC.; BRYAN, Marian C.; CHAN, Bryan; HANAN, Emily; HEFFRON, Timothy; PURKEY, Hans; ELLIOTT, Richard Leonard; HEALD, Robert; KNIGHT, Jamie; LAINCHBURY, Michael; SEWARD, Eileen M.; WO2014/81718; (2014); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application of 59489-71-3, The chemical industry reduces the impact on the environment during synthesis 59489-71-3, name is 2-Amino-5-bromopyrazine, I believe this compound will play a more active role in future production and life.

5-Bromopyrazin-2-amine (2.0 g, 11.49 mmol), (4-methylsulfonylphenyl)boronic acid (2.758 g, 13.79 mmol) and K3P04 (4.878 g, 22.98 mmol) were combined in MeCN (40 niL) / Water (10 mL) and Pd[P(tBu)3]2 (216 mg, 0.4227 mmol) was added. The reaction was heated at 60 C for 1 hour. The reaction mixture was cooled to ambient temperature and concentrated in vacuo. The residue was triturated with water, then Et20 then dried in vacuo to give the sub-title compound as a beige solid which was used without further purification (2.53 g, 88% Yield). 3H NMR (400.0 MHz, DMSO) delta 3.20 (s, 3H), 6.80 (br s, 2H), 7.94 (d, 2H), 8.00 (d, 1H), 8.17 (d, 2H) and 8.64 (d, 1H) ppm.

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, 2-Amino-5-bromopyrazine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; CHARRIER, Jean-Damien; DURRANT, Steven, John; YOUNG, Stephen, Clinton; STORCK, Pierre-Henri; VIRANI, Aniza, Nizarali; REAPER, Philip, Michael; PINDER, Joanne; WO2011/143423; (2011); A2;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Some common heterocyclic compound, 109-08-0, name is 2-Methylpyrazine, molecular formula is C5H6N2, 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. Recommanded Product: 2-Methylpyrazine

General procedure: Methyldiazine derivative (1mmol) and compound 3 (1.1equiv per methyl group) were dissolved in THF (20mL). tBuOK (1.5equiv per methyl group) was slowly added at room temperature. The solution, which immediately turned brown, was then refluxed overnight. After cooling, water was added, THF was evaporated and the mixture extracted with CH2Cl2, dried over MgSO4 and the solvent removed under vacuum.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 109-08-0, its application will become more common.

Reference:
Article; Achelle, Sylvain; Kahlal, Samia; Saillard, Jean-Yves; Cabon, Nolwenn; Caro, Bertrand; Robin-Le Guen, Franc?oise; Tetrahedron; vol. 70; 17; (2014); p. 2804 – 2815;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 4774-15-6, These common heterocyclic compound, 4774-15-6, name is 2,6-Dimethoxypyrazine, 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.

20 ml of 30% hydrogen peroxide was slowly added to 20 ml of acetic acid at room temperature, and then 4 g of 2,6-dimethoxypyrazine was added to the above oxidizing agent solution.After it is dissolved, the reaction system is heated to 55 C, and reacted for 4 hours; after the reaction is completed, the reaction system is cooled to room temperature and poured into ice water;The mixture was extracted 9 times with ethyl acetate.After the solid was filtered off, the filtrate was evaporated under reduced pressure to remove solvent.The white solid product 2,6-dimethoxypyrazine-4-oxide was obtained in a yield of 68%.

The synthetic route of 4774-15-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; China Engineering Physics Institute Chemical Materials Institute; Huang Qi; Li Hongzhen; Nie Fude; (11 pag.)CN107266376; (2017); A;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem