Pyrazines

Application of 13134-38-8,Some common heterocyclic compound, 13134-38-8, name is 3,6-Dimethylpyrazin-2-amine, molecular formula is C6H9N3, 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.

The obtained solution of O-(mesitylsulfonyl)hydroxylamine was added dropwise to a solution of 3,6-Dimethyl-pyrazin-2-ylamine (2.07 g, 1 1 .7 mmol) in DCM (100 mL) cooled in an ice bath. The mixture was then warmed to room temperature over 15 minutes. LCMS indicated almost complete conversion to the aminated intermediate. The solvent was evaporated and the residue was dissolved in Methanol (60 mL, 1000 mmol) followed by the addition of 1 ,8-Diazabicyclo[5.4.0]undec-7-ene (3.1620 mL, 21 .144 mmol) . The solution was stirred at RT for 5 mins where methyl 2- chloropropionate (1 .26 mL, 1 1 .7 mmol) was added and the solution stirred at RT for 48 hrs. The volatiles were removed in vacuo. Water was added and the organics extracted with EtOAc. The combined organics were washed with water, brine, dried (MgSO4) filtered and the volatiles removed in vacuo. The residue was purified by flash chromatography Eluent EtOAc:Heptane, 1 :1 and the product fractions collected and evaporated to yield 2-(1 -Chloro-ethyl)-5,8- dimethyl-[1 ,2,4]triazolo[1 ,5-a]pyrazine (1 .52 g; Yield = 61 .0%; Purity = 99.3%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3,6-Dimethylpyrazin-2-amine, its application will become more common.

Reference:
Patent; H. LUNDBECK A/S; KEHLER, Jan; KILBURN, John Paul; JESSING, Mikkel; NIELSEN, Jacob; WO2013/107856; (2013); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Related Products of 19847-12-2,Some common heterocyclic compound, 19847-12-2, name is Pyrazinecarbonitrile, molecular formula is C5H3N3, 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: 2-Cyanopyridine (0.420 ml; 4 mmol) was dissolved in absolute methanol (20 ml) and to it was added sodium methoxide solution in methanol (1.0 ml) (previously prepared). The reaction contents were stirred at room temperature for 2 h 1,4-diaminobutane (0.18 ml, 2 mmol) was added to the reaction mixture. Reaction contents were heated under reflux for 12 h. Solvent was removed under reduced pressure. Crude product so obtained was washed with diethyl ether and then with ethyl acetate to give thick mass. Solvent traces from this thick mass was removed by applying high vacuum for 15 min to give semisolid product i.e. N-(2-pyridineimidoylamino-butyl)-pyridine-2-carboxamidine (5a). Yield 480 mg (81%).

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

Reference:
Article; Arya, Surbhi; Kumar, Nikhil; Roy, Partha; Sondhi; European Journal of Medicinal Chemistry; vol. 59; (2013); p. 7 – 14;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 369638-68-6, 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. 369638-68-6, name is tert-Butyl (5-methylpyrazin-2-yl)carbamate belongs to pyrazines compound, it is a common compound, a new synthetic route is introduced below.

tert-butyl 5-methylpyrazin-2-yl carbamate (6.27 g, 30.0 mmol) was weighed and dissolved in 30 mL dichloromethane, and in an ice water bath, 20 mL trifluoroacetic acid was added slowly. It was moved to react at room temperature for 1 hour, rotate evaporated to dryness to remove the solvent, and was used for the next step directly.

The synthetic route of tert-Butyl (5-methylpyrazin-2-yl)carbamate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; KBP Biosciences Co., Ltd.; ZHANG, Yan; ZHANG, Min; LO, HoYin; (52 pag.)EP2781508; (2014); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

875781-43-4, name is 2-Bromo-5H-pyrrolo[2,3-b]pyrazine, 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. category: Pyrazines

2-bromo-5H- pyrrolo [2,3-b] pyrazine (5.0g, 25.2 mmol) of 1,4-dioxane (100mL) 2.0M NaOH aqueous solution to the partial suspension in (25mL, 50 2.0 mmol) and 37% formaldehyde aqueous solution (19mL, 252 mmol) was added. The reaction mixture of this dark homogeneous mixture was stirred overnight at room temperature. The organics were evaporated under reduced pressure. The aqueous layer was neutralized with 1.0 M HCl, and extracted with EtOAc (2x). And the combined organics concentrated to give a solid orange 2.6 g. When allowed to stand, thick brown precipitate formed in the aqueous layer. This precipitate was collected by filtration, and dried. And extracted with the hot brown solid 10% MeOH / EtOAC (3x200mL). The extracts are combined and evaporated to give an additional solid orange 3.05 g. The entire yield, 5.65g (87%) (2-bromo-7-hydroxymethyl-pyrrolo [2,3-b] pyrazin-5-yl)-methanol.

The synthetic route of 875781-43-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F.HOFFMANN-LA ROCHE AG; HENDRICKS, ROBERT THAN; HERMANN, JOHANNES CORNELIUS; KONDRU, RAMA K; LOU, YAN; LYNCH, STEPHEN M; OWENS, TIMOTHY D; SOTH, MICHAEL; (50 pag.)JP5667692; (2015); B2;,
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Pyrazine | C4H4N2 – PubChem

Application of 6705-33-5, 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. 6705-33-5, name is Pyrazin-2-ylmethanol, This compound has unique chemical properties. The synthetic route is as follows.

Methanesulphonyl chloride (171 . 1, 2.21 mmol) was added dropwise to a solution of 2- (hydroxymethyl) pyrazine (221 mg, 2.01 mmol) and N-DIISO-PROPYLETHYLAMINE (385 ZL, 2.21 mmol) in DCM (10 ml). The mixture was heated to 40C for 1 hour. The reaction mixture was concentrated in vacuo and the residue was dissolved in dry DMA (5 ml). This solution was added to a mixture of 2-chloro-4-({5-[(1S)-2-(dimethylamino)-1- methylethoxy] quinazolin-4-yl} amino) phenol (0.5 g, 1.34 mmol), potassium carbonate (0.93 g, 6.7 mmol) and 18-crown-6 (20 mg) in dry DMA (20 ml). The reaction mixture was stirred at ambient temperature overnight. Water (500 ml) was added to the mixture and the resultant precipitate was filtered. This was crystallised from ethyl acetate to give two batches of crystals with a combined weight of 261 mg (42%); NMR spectrum (CDC13) ; 1.46 (d, 3H), 2.23 (s, 6H), 2.40 (dd, 1H), 2.86 (dd, 1H), 4.61-4. 74 (m, 1H) 5.25 (s, 2H), 6.85 (d, 1H), 6. 98 (d, 1H), 7.37 (d, 1H), 7.55 (t, 1H), 7.68 (d, 1H), 7.73 (s, 1H), 8.50 (s, 2H), 8.54 (s, 1H), 8.92 (s, 1H), 10.32 (s, 1H) ; Mass spectrum MHF 465.; Example 38 5-R2- (DIMETHYLAMINO) ETHOXVL-N-R3-METHOXV-4- (NVRAZIN-2-VLMETHOXV) PHENVLLQUINAZOLIN- 4-amine Methanesulphonyl chloride (26 JELL, 0.33 mmol) was added dropwise to a solution of 2- (hydroxymethyl) pyrazine (33 mg, 0.30 MMOL) AND N, N-DIISO-PROPYLETHYLAMINE (57, UL, 0.33 mmol) in DCM (2 ml). The mixture was heated to 40C for 2 hours. The solvent was evaporated, and the residue dissolved in DMA (1 ml). This solution was added to a mixture of 4-({5-[2-(DIMETHYLAMINO) ethoxy] QUINAZOLIN-4-YL} AMINO)-2-METHOXYPHENOL (obtained as described in Example 20, preparation of starting materials, 71 mg, 0.20 mmol), potassium carbonate (138 mg, 1.00 MMOL), and 18-crown-6 (20 mg) in DMA (10 ml). The mixture was briefly sonicated, and was stirred at room temperature for 48 hours. The solvent was removed in vacuo, and the residue was partitioned between DCM (15 ML) and water (15 ml). The DCM layer was loaded onto a silica column; the column was eluted with 2 to 4% (10: 1 MEOH/CONC. NH3 (AQ)) in DCM. Evaporation of the appropriate fractions followed by crystallisation from methyl TERT-BUTYL ether gave the title compound as a white crystalline solid (53 mg, 59% yield). NMR spectrum (DMSO-d6); 2.25 (s, 6H), 2.80 (t, 2H), 3.84 (s, 3H), 4.37 (t, 2H), 5.26 (s, 2H), 7.12 (d, 1H), 7.15 (d, 1H), 7.22 (dd, 1H), 7.33 (d, 1H), 7.62 (d, 1H), 7.72 (dd, 1H), 8.47 (s, 1H), 8.64 (d, 1H), 8.68 (dd, 1H), 8. 83 (d, 1H), 10.39 (s, 1H); Mass spectrum MH 448.

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

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2004/93880; (2004); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Related Products of 36070-79-8, 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 36070-79-8 as follows.

General procedure: 150 mg (0.952 mmol) of 5-Cl-PZA (1) or 6-Cl-PZA (2) was dissolved in ethanol together with triethylamine (1 eq., 96 mg, 0.952 mmol). Three equivalents of corresponding alkylamine were added to the reaction mixture and refluxed in ethanol generally for 6 hours. The completion of the reaction was checked by TLC chromatography (eluent: hexane/ethyl acetate, 1:2). The crude product was absorbed on silica by solvent evaporation and purified by flash chromatography (hexane/ethyl acetate gradient elution).

According to the analysis of related databases, 36070-79-8, the application of this compound in the production field has become more and more popular.

Reference:
Article; Servusova, Barbora; Paterova, Pavla; Mandikova, Jana; Kubicek, Vladimir; Kucera, Radim; Kunes, Jiri; Dolezal, Martin; Zitko, Jan; Bioorganic and Medicinal Chemistry Letters; vol. 24; 2; (2014); p. 450 – 453;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Some common heterocyclic compound, 312736-49-5, name is 3,5-Dichloropyrazine-2-carboxylic acid, molecular formula is C5H2Cl2N2O2, 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. Computed Properties of C5H2Cl2N2O2

To a stirred heterogeneous mixture of 3,5-dichloropyrazine-2-carboxylic acid (2.21 g, 11.5 mmol) in anhydrous CH2Cl2 (20 mL), thionyl chloride (7.5 mL, 103 mmol) was added under an atmosphere of nitrogen, followed by anhydrous DMF (30 mg, 0.41 mmol) and the reaction mixture was stirred at room temperature for 1 hour. The reaction mixture was evaporated, dissolved in CH2Cl2 (40 mL) and added dropwise to a solution of 6-nitropyridine-2-sulfonamide (2.32 g, 11.5 mmol) with triethylamine (8.5 mL, 61.0 mmol) at 0 C., stirred overnight (24 h) while allowing to warm to ambient temperature. The reaction mixture was concentrated under reduced pressure. The residue was partitioned between CH2Cl2 (10 mL) and ice-water (200 mL) and acidified with 2 M HCl to pH about 4.0. The resulting solid was filtered, the layers separated and the aqueous layer was extract with CH2Cl2 (3×50 mL). The combined organics were washed sequentially with 1N HCl, saturated sodium chloride solution then dried over sodium sulfate, filtered and evaporated under reduced pressure. The crude material was purified by triturating with dichloromethane (10 mL), filtration and drying to give 3,5-dichloro-N-[(6-nitro-2-pyridyl)sulfonyl]pyrazine-2-carboxamide (2.90 g, 67%) as a white solid. ESI-MS m/z calc. 376.93884. found 378.0 (M+1)+. Retention time: 0.6 minutes.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 312736-49-5, its application will become more common.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; Miller, Mark Thomas; Anderson, Corey; Arumugam, Vijayalaksmi; Bear, Brian Richard; Binch, Hayley Marie; Clemens, Jeremy J.; Cleveland, Thomas; Conroy, Erica; Coon, Timothy Richard; Frieman, Bryan A.; Grootenhuis, Peter Diederik Jan; Gross, Raymond Stanley; Hadida-Ruah, Sara Sabina; Haripada, Khatuya; Joshi, Pramod Virupax; Krenitsky, Paul John; Lin, Chun-Chieh; Marelius, Gulin Erdgogan; Melillo, Vito; McCartney, Jason; Nicholls, Georgia McGaughey; Pierre, Fabrice Jean Denis; Silina, Alina; Termin, Andreas P.; Uy, Johnny; Zhou, Jinglan; (590 pag.)US2016/95858; (2016); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Related Products of 762240-92-6, 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. 762240-92-6, name is 3-(Trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine hydrochloride belongs to pyrazines compound, it is a common compound, a new synthetic route is introduced below.

N,N-dimethylformamide (96.0 L) to (3R)-3-[N-(tert-butoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoic acid (12.00 kg) and 3-(trifluoromethyl)-5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-alpha]pyrazine hydrochloride (9.05 kg) was added, stirring and the temperature was cooled to -5 C to 0 C. N-methylmorpholine (4.01 kg) and 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide hydrochloride (8.28 kg) were added, After stirring for 1 hour at -5 C to 0 C and warmed to 20 C to 25 C and stirred for 3 hours. Ethyl acetate (192.0 L) and purified water (96.0 L) were added to the reaction mixture, which was then stirred for 10 minutes. The organic layer was separated, and the separated water layer was extracted with ethyl acetate (48.0 L) once more for 10 minutes to collect the organic layers. The combined organic layer was washed successively with 5% aqueous sodium carbonate solution and washed with a (sodium carbonate: 96.0 L: 4.8 kg, purified water). Dehydrated with anhydrous magnesium sulfate (12.0 kg) for 10 minutes, filtered and washed with ethyl acetate (24.0 L) and concentrated under reduced pressure. cyclohexane (240.0 L) was put into the obtained residue, and it stirred at 70 degreeC-72 degreeC for 5 minutes. After cooling to 20 to 25 stirred for 1 hour, filtered and washed with cyclohexane (36.0 L). Vacuum drying at 40 C to 45 C. the desired compound 7-[(3R)-3-[(N-tert-butoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoyl]-3-(trifluoromethyl)-5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-alpha]pyrazine (15.70 kg, yield : 85.9%) was obtained.

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-(Trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine hydrochloride, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Most Medicine Co., Ltd.; Hong Seung-min; Shin So-yeong; Kang Seok-won; (10 pag.)KR2019/60235; (2019); A;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application of 33332-25-1, 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. 33332-25-1, name is Methyl 5-chloropyrazine-2-carboxylate belongs to pyrazines compound, it is a common compound, a new synthetic route is introduced below.

A solution of methyl 5-chloropyrazine-2-carboxylate (1.0 g, 5.79 mmol) and morpholine (756 mg, 8.69 mmol) in DMSO (10 mL) was added K2C03(2.4 g, 17.4 mmol). The mixture washeated to 100 C for 4 hours and then cooled to r.t. Water (20 mL) was added and the mixture was extracted with EA(20 mLx3).The combined organic phase was washed with water (20 mL) and brine (20 mL).It was then dried over anhydrous Na2SO4 and concentrated to give the desired product as a yellow solid (850 mg) which was used directly next step. ESI-MS m/z:224.1 [M+Hj.

The synthetic route of Methyl 5-chloropyrazine-2-carboxylate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ENANTA PHARMACEUTICALS, INC.; SHOOK, Brian, C.; KIM, In, Jong; BLAISDELL, Thomas, P.; YU, Jianming; PANARESE, Joseph; OR, Yat, Sun; (434 pag.)WO2017/15449; (2017); A1;,
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Pyrazine | C4H4N2 – PubChem

Reference of 19847-12-2, The chemical industry reduces the impact on the environment during synthesis 19847-12-2, name is Pyrazinecarbonitrile, I believe this compound will play a more active role in future production and life.

To a solution of sodium methoxide (NaOCH3) (51.4 g, 0.952 mol) in methanol (3800 ml) there is added cyanopyrazine (1.00 KG, 9.53 mol) slowly at room temperature. The mixture is heated to 30 C. and stirred for 6 h. The mixture is cooled to 25 C. followed by the addition of ammonium chloride (NH4Cl) (572 g, 10.5 mol). The reaction mixture is stirred for 22 h and methyl t-butyl ether (4000 mL) is added and the mixture is stirred for 15 min forming a solid. The solid is filtered and washed with methyl t-butyl ether (2×1000 mL) then dried at 40 C./0-10 mmHg for 17 h to give white solid product (1435 g) in 95% yield with 95% HPLC purity. 1H NMR (DMSO-D6): delta 9.7 (bs, 3H), 9.49 (d, 1H, J=1.5 Hz), 9.04 (m, 1H), 8.93 (t, 1H, J=1.5 Hz)

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, Pyrazinecarbonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Wyeth; US2006/281760; (2006); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem