Category: 33332-28-4

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. 33332-28-4, name is 2-Amino-6-chloropyrazine belongs to pyrazines compound, it is a common compound, a new synthetic route is introduced below. COA of Formula: C4H4ClN3

6-Chloro-5-iodo-4-ylpyrazin-2-amine To a O0C cooled stirred solution of 2-amino-6-chloropyrazine (3 g, 23 mmol) in a mixture of DMSO (90 mL) and water (2.2 mL), was added Lambda/-iodosuccinimide (5.2 g, 23 mmol) in EPO portions. After stirring for 72h, the mixture was poured into water, extracted twice with ethyl acetate, the organic layers washed with brine, dried (MgSO4) and evaporated. Flash chromatography (98:2 dichloromethane/methanol) furnished the title compound as a yellow solid (4.43 g, 76%). delta 1H-NMR (CDCI3): 7.73 (s, 1H), 4.72 (s, 2H).ESI/MS (m/e, %): 255 [(M+1) C4H3CIIN3].

The synthetic route of 33332-28-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ALMIRALL PRODESFARMA, S.A.; WO2007/17096; (2007); 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. 33332-28-4, name is 2-Amino-6-chloropyrazine, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 33332-28-4

To a solution of 6-chloro-pyrazin-2-ylamine (5.0 g, 38.8 mmol) in chloroform (194 mL) was added N-bromosuccinimide (20.7 g, 116 mmol) under a nitrogen atmosphere and the reaction mixture was stirred at room temperature for 5 h. The resulting mixture was poured into an aqueous solution of K2CO3 (300 mL) and extracted with dichloromethane (200 mL x 4). The combined organic extracts were dried and purified by chromatography (silica, 10-20 percent ethyl acetate in hexanes) to give 3,5-dibromo-6-chloro-pyrazin-2-ylamine (4.2 g, 38percent) as a yellow solid. LC-MS: 286.0 (M-H).

According to the analysis of related databases, 33332-28-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; HERMANN, Johannes Cornelius; KENNEDY-SMITH, Joshua; LUCAS, Matthew C.; PADILLA, Fernando; SCHOENFELD, Ryan Craig; WOVKULICH, Peter Michael; WO2014/29732; (2014); 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. 33332-28-4, name is 2-Amino-6-chloropyrazine, A new synthetic method of this compound is introduced below., Application In Synthesis of 2-Amino-6-chloropyrazine

A. 6-Methylpyrazine-2-ylamine. To a solution containing 6-chloro-2- pyrazineamine (5.0 g, 38.75 mmol) in 1,4-dioxane (70 mL) was added [1,3- bis(diphenylphosphino]Ni(II)Cl2 (2.10 g, 38.76 mmol), followed by drop-wise addition of dimethylzinc in toluene (38.75 mL, 2.0 M, 77.50 mmol), over 15 min. The solution was allowed stir at 105 °C for 16 hours. The solution was then condensed under reduced pressure, diluted with ethyl acetate and filtered through celite to remove the nickel salts. The resultant slurry was purified via Biotage silica gel chromatography (0-8percent methanol in dichloromethane) to afford the title compound as an orange solid (1.18 g, 28percent yield). MS (ESI) m/z 1 10.3 [M+ 1]+.

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; SIGNAL PHARMACEUTICALS, LLC; WO2008/51493; (2008); A2;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 33332-28-4, A common heterocyclic compound, 33332-28-4, name is 2-Amino-6-chloropyrazine, molecular formula is C4H4ClN3, 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.

Dimethylzinc (lOOmL of a 2M solution in toluene) was added dropwise over 0.5h to astirred solution of 6-chloro-2-pyrazinamine (12.9g) and [1,3-fe(diphenylphosphmo)propane]nickel(n) chloride (5.4g) in dioxane (200mL) under anitrogen atmosphere. The reaction mixture was heated at reflux for 18h, then cooled toroom temperature and quenched cautiously with zso-propanol (30mL) and methanol(50mL). After removal of solvent in vacua, the residue was partitioned betweendichloromethane and aqueous ammonium chloride. The organic phase was filtered throughcelite, dried (MgSO4), filtered and evaporated to give the crude product as an orange solid.Chromatography on silica gel eluting with ethyl acetate/methanol mixtures gave the sub- title compound (5.1g). Used directly.

The synthetic route of 33332-28-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTRAZENECA AB; WO2004/108692; (2004); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

These common heterocyclic compound, 33332-28-4, name is 2-Amino-6-chloropyrazine, 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. Recommanded Product: 2-Amino-6-chloropyrazine

A solution of 6-chloropyrazin-2-amine (2 g, 15.44 mmol) and N BS (13.7 g, 77 mmol) in CHCI3 (100 ml) was heated at reflux for 20 hours. The resulting mixture was purified bychromatography on silica eluting with DCM. The relevant fractions were concentrated in vacuo and the crude product was dissolved in EtOAc (~100 ml), washed with 10 percent sodium thiosulfate (2 x 100 ml), brine, dried (MgS04) and were concentrated in vacuo to afford the title compound; 1 H NMR (400 MHz, CDCI3) delta 5.4-5.0 (2H, br s).

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

Reference:
Patent; NOVARTIS AG; CHARLTON, Steven, John; LEBLANC, Catherine; MCKEOWN, Stephen, Carl; WO2012/7539; (2012); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 33332-28-4, name is 2-Amino-6-chloropyrazine, 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 33332-28-4, HPLC of Formula: C4H4ClN3

6-Morpholinop razin-2-amineA stirred solution of 6-chloropyrazin-2-amine (0.225 g, 1.74 mmol) and morpho- line (0.227 g, 2.61 mmol) was heated at 100 C for 22 h. After cooling to 23 C, water was added to the mixture and extracted with EtOAc. The combined organics were concentrated in vacuo. The crude mixture was purified on alumina (0-50% EtOAc in hexane) to give the desired product 6-morpholinopyrazin-2- amine. Mass Spectrum (ESI) m/e = 181.1 (M + 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, 2-Amino-6-chloropyrazine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; AMGEN INC.; DRANSFIELD, Paul John; GONZALEZ LOPEZ DE TURISO, Felix; PATTAROPONG, Vatee; SIMARD, Jillian L.; WO2012/3264; (2012); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 33332-28-4, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 33332-28-4 name is 2-Amino-6-chloropyrazine, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

Example 29: Preparation of:2-(4-Ch]oro-2-mophiholin-4-yl-1.24hiazol-5-yl)-5-(dicvcloprorhoyImethylV3,7-dimethyl-5H-pyitauolof2.3- ipyrazine; Part A: 2-Amino-6-methy] pyrazine; A solution of zinc chloride (2.0M in THF, 96.5 mL, 48.2 mmol, 5.0 equiv.) is treated dropwise with methylmagnesium bromide (3.0 M in Et2O, 32.2 mL, 96.5 mmoi, 10.0 equiv.) at 0 °C. The mixture is wanned to room temp and stirred for 45 min. A solution of 2-amino-6-chloro pyrazine (1.25 g. 9.65 mmol, 1.0 equiv) and NiC12(dppp) (157 mg, 0.29 mmol, 0.03 equiv) in THF (15 mL) is added to the freshly prepared dimethylzinc reagent. The reaction mixture is stirred under for 3h and cooied to room temp. The reaction is quenched carefully with sat’d NH4CI solution and allowed to stir overnight. The layers are separated and the aqueous layer is extracted with EtOAc (2 X 30 mL). The combined organic extracts are washed with brine, dried over Na2Spsi4 and concentrated under reduced pressure to give a cream-colored solid that is used without further purification. MS = 110.08 (M +1). 1H NMR (400 MHz, CDCI3) delta 7.78 (IH, s), 7.72 (IH, s), 4.59 (2H, bs), 2.35 (3H, s).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Amino-6-chloropyrazine, and friends who are interested can also refer to it.

Reference:
Patent; NEUROGEN CORPORATION; WO2008/83070; (2008); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application of 33332-28-4,Some common heterocyclic compound, 33332-28-4, name is 2-Amino-6-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.

EXAMPLE 4A 6-(allyloxy)-2-pyrazinamine A mixture of allyl alcohol (0.21 mL, 3.08 mmol) in dioxane (4 mL) was treated with NaH (60percent, 3.08 mmol), stirred for 30 minutes, treated with 2-amino-6-chloropyrazine (200 mg, 1.54 mmol), heated to 140° C. in a Smith Synthesizer for 2200 seconds, and filtered. The filtrate was concentrated and purified by flash column chromatography eluding with hexanes/ethyl acetate (2:1) to provide the desired product (133 mg, 57percent). MS (DCI/NH3) m/z 152.0 (M+H)+; 1H NMR (500 MHz, CD2Cl2) delta 4.75 (m, 2H), 5.24 (m, 1H), 5.37 (m, 1H), 6.05 (m, 1H), 7.50 (s, 1H), 7.53 (s, 1H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Amino-6-chloropyrazine, its application will become more common.

Reference:
Patent; Tao, Zhi-Fu; Lin, Nan-Horng; Wang, Le; Sowin, Thomas J.; US2005/96324; (2005); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 33332-28-4, 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. 33332-28-4, name is 2-Amino-6-chloropyrazine, This compound has unique chemical properties. The synthetic route is as follows.

[l-(tert-butoxycarbonyl)-lH-indol-2-yl]boronic acid (2.22 g, 8.49 mmol), 6- chloropyrazin-2-amine (1.00 g, 7.72 mmol), K2CO3 (2.67 g, 19.3 mmol) and Pd(PPh3)4 (180 mg, 0.15 mmol) were mixed in MeCN/water (3.5: 1) and stirred at 85 0C for 20 hours. The reaction mixture was concentrated and the residue was extracted with EtOAc (2x 40 mL) and water (50 mL). The organic layers were combined, dried (Na2SO^, filtered and concentrated to give 2.5 g of a brown solid of tert-butyl 2-(6-aminopyrazin-2-yl)- lH-indole-l-carboxylate. The material was used in the next step without further purification. To tert-butyl 2-(6-aminopyrazin-2-yl)-lH-indole- l-carboxylate (1.1 g, 3.5 mmol) in dry toluene (10 mL) were added methyl 6-chloronicotinate (0.67 g, 3.90 mmol), K2CO3 (7.35 g, 53.2 mmol), (+/-)-BINAP (0.1 1 g, 0.18 mmol) and Pd(OAc)2 (40 mg, 0.18 mmol). The mixture was re fluxed for 50 minutes. The solvent was evaporated and the residue was extracted with EtOAc (2×100 mL) and washed with water/brine (1 : 1 ; 100 mL). The organic layers were combined, dried (Na2Spsi4), filtered and concentrated to give 2 g of crude product. Purification was performed by flash chromatography (1percent NEt3 in DCM-> 1percent NEt3, 1percent MeOH in DCM). This gave tert-butyl 2-(6-{[5-(methoxycarbonyl)pyridin-2- yl]amino}pyrazin-2-yl)-lH-indole- l-carboxylate (620 mg). The material was divided into four microwave tubes (155 mg, 0.35 mmol in each) and dissolved in MeOH. 2M aq NaOH (0.35 mL, 0.70 mmol) was added and the reaction mixture was irradiated in a microwave oven at 1 10 0C for 15 minutes. 6M aq HCl (0.12 mL, 0.70 mmol) was added. The reactions were combined and concen- trated in vacuo to give the crude title compound as a brown solid (720 mg). MS (ESI+) for C18H 13N5O2 m/z 332 (M+H)+.

The chemical industry reduces the impact on the environment during synthesis 2-Amino-6-chloropyrazine. I believe this compound will play a more active role in future production and life.

Reference:
Patent; BIOVITRUM AB (PUBL); WO2007/147874; (2007); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 33332-28-4, These common heterocyclic compound, 33332-28-4, name is 2-Amino-6-chloropyrazine, 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.

Synthesis 2-1 -B 5-bromo-6-chloropyrazin-2-amine 6-Chloropyrazin-2-amine (2.50 g, 19.3 mmol) was stirred in dichloromethane (60 mL) and cooled to OC. N-Bromosuccinimide (2.92 g, 16.4 mmol) was added slowly and the reaction mixture was stirred at 0C for 60 minutes. The reaction mixture was filtered through celite and concentrated to give a brown oil. Purification by flash chromatography, eluting with 0-25% ethyl acetate-hexane, gave the title compound as a yellow solid (1.69 g, 8.16 mmol, 42%). 1HMR (d6-DMSO, 400 MHz) delta 7.65 (s, 1H), 7.1 (br s, 2H). LC-MS (1) rt 1.46 min; m/z (ESI-) 205 (M-H).

The synthetic route of 33332-28-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CANCER RESEARCH TECHNOLOGY LIMITED; WO2009/103966; (2009); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem