Tag: M.W=100-200

Electric Literature of 74290-68-9, These common heterocyclic compound, 74290-68-9, name is 6-Bromo-5-methylpyrazin-2-amine, 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.

(4-Methoxy-2-methylphenyl)boronic acid (104 mg, 0.63 mmol), was combined with 6-bromo-5-methylpyrazin-2-amine (98 mg, 0.52 mmol) andtetrakis(triphenylphosphine)palladium(0) (31.6 mg, 0.03 mmol) in 1,4-dioxane (2 mL) and the reaction mixture was degassed with nitrogen. To this solution was added a degassed solution of sodium carbonate (166 mg, 1.56 mmol) in water (0.6 mL). After being heated in a microwave reactor at 130 00 for 2 hours, the reaction mixture was concentrated in vacuo. Purification via silica gel chromatography (Gradient: 40% to100% ethyl acetate in heptane) provided the product as a white solid. Yield: 111 mg,0.48 mmol, 93%. LCMS m/z 230.1 [M+H]. 1H NMR (400 MHz, CD3OD) oe 7.85 (5, 1H),7.08 (d, J=8.4 Hz, 1H), 6.87 (d, J=2.5 Hz, 1H), 6.84 (dd, J=8.0, 2.3 Hz, 1H), 3.82 (5,3H), 2.13 (5, 3H), 2.09 (5, 3H).

The synthetic route of 74290-68-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PFIZER INC.; GRAY, David Lawrence Firman; DAVOREN, Jennifer Elizabeth; DOUNAY, Amy Beth; EFREMOV, Ivan Viktorovich; MENTE, Scot Richard; SUBRAMANYAM, Chakrapani; WO2015/166370; (2015); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 213019-67-1, name is 3-(Trifluoromethyl)pyrazin-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 213019-67-1, Product Details of 213019-67-1

A solution of bromine in dichloromethane (10ml) was added in portions to a stirred solution of 2-amino-3-trifluoromethylpyrazine (1.5g, 9.2mmol) and pyridine (0.90ml, 1 1 mmol) in chloroform. The resulting mixture was stirred at room temperature for 24 hours. Volatiles were removed under reduced pressure and the residue was purified by chromatography on silica gel using a gradient of ethyl acetate in isohexane as eluent to give 2-amino-3-trifluoromethyl-5-bromopyrazine (1 .7g, 77%) as an off-white solid. (0286) 1H NMR (400MHz, CDCI3) delta 8.30 (s, 1 H), 5.13 (br s, 2H).

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Reference:
Patent; SYNGENTA PARTICIPATIONS AG; WAILES, Jeffrey, Steven; CARTER, Neil, Brian; CLOUGH, John, Martin; WILLIAMS, John; (57 pag.)WO2019/57723; (2019); 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 77168-85-5 as follows. Quality Control of Methyl 5-chloro-6-methylpyrazine-2-carboxylate

[0145j A solution of methyl 5-chloro-6-methylpyrazine-2-carboxylate (1 g, 5.37 mmol) and potassium trimethyl silanolate (1.3 g, 10.7 mmol) in tetrahydrofuran (15 mL) was stirred at 70 °C under microwave irradiation for 20 minutes. Then the reaction mixture was acidified with iN hydrochloric acid to pH 3 and extracted with ethyl acetate (100 mL x 2). The combined organic extract was washed with brine (200 mL), dried over sodium sulfate and concentrated under vacuum to afford the title compound 5-chloro-6-methylpyrazine-2- carboxylic acid (0.800 g, crude) as a light yellow solid which was used for next step without further purification. Calculated M+H: 173.03; Found M+H: 173.33.

According to the analysis of related databases, 77168-85-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MNEMOSYNE PHARMACEUTICALS, INC.; ANDERSON, David R.; VOLKMANN, Robert A.; WO2015/48503; (2015); A2;,
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. 5521-61-9, name is 6-Methylpyrazine-2-carboxylic acid, A new synthetic method of this compound is introduced below., Application In Synthesis of 6-Methylpyrazine-2-carboxylic acid

Step 2: methyl 5-(6-methylpyrazine-2-carboxamido)bicyclo[3.2.11 octane-l-carboxylateTo a solution of methyl 5-aminobicyclo[3.2.1 ]octane- l -carboxylate (0.98 g, 5.36 mmol) and 6-methylpyrazine-2-carboxylic acid (0.89 g, 6.45 mmol) in DCM (30 mL) and TEA (2 mL) was added PyBOP (3.35 g, 6.44 mmol). After stirring at room temperature overnight, water (30 mL) was added and the mixture was extracted with DCM (3 x 50 mL). The combined organic layer was washed with Sat. NaHC0 (50 mL) and brine (50 mL), dried over a2S04 and concentrated under reduced pressure. The residue was purified by column chromatography (silica gel, petroleum ether/ethyl acetate: 1/1 ) to afford 1 .28 g (79percent) of methyl 5-(6-methylpyrazine-2-carboxamido)bicyclo[3.2.1]octane-l -carboxylate as an off- white solid. ESI-MS m/z: 304 (M+H)+.

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

Reference of 5910-89-4, These common heterocyclic compound, 5910-89-4, name is 2,3-Dimethylpyrazine, 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.

The S-2-[3-(3-methylpyrazin-2-yl)isoxazol-5-yl]pyrrolidine starting material was prepared as follows: A mixture of 2,3-dimethylpyrazine (2Og, 18.5mmol), selenium dioxide (41.06g,25 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 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) and30 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- EPO 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).

The synthetic route of 5910-89-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2006/109026; (2006); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 77168-85-5, These common heterocyclic compound, 77168-85-5, name is Methyl 5-chloro-6-methylpyrazine-2-carboxylate, 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.

Water (500ml) and Compound ll-a (85.0 g) were changed into a flask and the mixture was agitated for 10 to 20 minutes. Potassium Phosphate (127g) and toluene (500ml) were charged into the reaction. The batch was agitated until all solids were dissolved. The aqueous was split and the organic phase was concentrated to about 170ml or less if possible under vacuum. 1-Methyl-2- pyrrolidinone (NMP) (204 ml) was charged to the batch, which was further concentrated to about 300 ml under vacuum. The batch was cooled to below O0C. To the batch, Compound ll-b (5Og) and N, N diisopropylethylamine (60ml) were charged. The batch was heated to 9O0C for about 17 hours unti. the reaction was completed. The batch was concentrated under vacuum at 8O0C until no distillate came out. The batch was cooled to 20 0C. Water (255 ml) and TBME (510 ml) were added into the batch. The mixture was agitated and phases were separated in a separation funnel. The organic layer was washed again with 250 ml of water. The combined aqueous layer was back extracted with 200 ml of TBfVIE. The combined organic iayer was washed with 0.5N HCi (100 ml). The batch was concentrated at vacuum unti. 255ml TBME (510 mi) was charged info the batch and concentrated to 250 mi. After cooling to Q- 1O0C, a solution of 2-isopropanol hydrochloride solution (5-6N1 170ml) was added under 250C and the solution was agitated at 15-25 0C for 20 hours. TBME (255 ml) was charged into the batch and agitated at 25 0C for 2 hours. The batch was filtrated and washed with a mixture of T8ME/2-Isopropanol. (200 ml, 2/1 v/v). The wet cake was dried at vacuum oven at 50 0C to give 65.0 g (77percent) of the white solid. 1H NMR(400 MHz in CD3OD): 8.86 (S5 1 H)1 4.83(S, 2H), 3.94(m, 4H); 3.53 (m, 3H); 3.24 (t, 1 H); 2.99 (dd, 1 H); 2.66 (S5 3H)1 1.82 (m, 2H); 1.11 (m, 6H). 13C NMR (400 Mhe, CD3OD): delta 165.3; 160.4; 152.4;143.3; 139.2′ 58.3; 53.8; 53.8; 51.5; 49.9, 25.1 ; 21.4; 17.1 , 10.6.

Statistics shows that Methyl 5-chloro-6-methylpyrazine-2-carboxylate is playing an increasingly important role. we look forward to future research findings about 77168-85-5.

Reference:
Patent; SCHERING CORPORATION; WO2009/79490; (2009); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 5910-89-4, A common heterocyclic compound, 5910-89-4, name is 2,3-Dimethylpyrazine, molecular formula is C6H8N2, 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.

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 700C for 220 hours. The mixture was allowed to cool and the insoluble matter was removed by filtration 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 at25 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).

The synthetic route of 5910-89-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2006/100461; (2006); 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. 213019-67-1, name is 3-(Trifluoromethyl)pyrazin-2-amine, This compound has unique chemical properties. The synthetic route is as follows., name: 3-(Trifluoromethyl)pyrazin-2-amine

To 3-(trifluoromethyl)pyrazin-2-amine (0.020 g, 0.12 mmol, Oakwood) in CH2Cl2 (0.5 mL) was added N-bromosuccinimide (0.022 g, 0.12 mmol) and the reaction was stirred overnight. The reaction mixture was partitioned between DCM and water, and the aqueous portion was extracted with three portions of DCM. The combined organic extracts were dried over Na2SO4, filtered, and concentrated. The product was purified by flash chromatography, eluting with a gradient from 0-25% EtOAc in hexanes to afford a white crystalline solid (0.013 g, 44%). 1H NMR (400 MHz, CDCl3) delta 8.44-8.23 (s, 1H), 5.22-4.98 (s, 2H). 19F NMR (376 MHz, CDCl3) delta -65.04–69.69 (s).

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 213019-67-1.

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

Reference of 38557-71-0, These common heterocyclic compound, 38557-71-0, name is 2-Chloro-6-methylpyrazine, 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.

To a suspension of 2-chloro-6-methylpyrazine (24 g, 186.7 mmol) in anhydrous MeOH (240 mL) was added NaOMe (12.1 g, 224 mmol). The mixture was stirred at 60-70C for 16 hours. The mixture was cooled and filtered. The filtrate was concentrated in vacuo to give 2- methoxy-6-methylpyrazine (22 g, 95% yield). H NMR (CDCI3400 MHz): (5 7.98 (s, 1 H), 7.94 (s, 1 H), 3.91 (s, 3H), 3.40 (s, 3H). LC-MS: tR = 1.47 min (method 14), m/z = 124.8 [M + H]+.

Statistics shows that 2-Chloro-6-methylpyrazine is playing an increasingly important role. we look forward to future research findings about 38557-71-0.

Reference:
Patent; H. LUNDBECK A/S; KEHLER, Jan; RASMUSSEN, Lars, Kyhn; LANGGARD, Morten; JESSING, Mikkel; VITAL, Paulo, Jorge, Vieira; JUHL, Karsten; (159 pag.)WO2018/78042; (2018); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

These common heterocyclic compound, 77168-85-5, name is Methyl 5-chloro-6-methylpyrazine-2-carboxylate, 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. SDS of cas: 77168-85-5

A mixture of methyl 5-chloro-6-methylpyrazine-2-carboxylate (3.00 g, 16.1 mmol), 2,2,2-trifluoroethanol (32.2 g, 322 mmol), and potassium carbonate (3.33 g, 24.1 mmol) in DMF (30 mL) is stirred at 60 oC for 2 hours. After cooling to rt, the mixture is filtered off, and the filtrate is diluted with EtOAc (300 mL). The organic layer is washed with water (100 mLx3) and dried over sodium sulfate. After filtration, the filtrate is concentrated in vacuo. The residue is purified by column chromatography on silica gel eluting EtOAc to give 3.91 g (97 percent yield) of the title compound as a white solid. MS (ESI) m/z: 251 (M+H) +.

The synthetic route of Methyl 5-chloro-6-methylpyrazine-2-carboxylate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; RAQUALIA PHARMA INC.; YAMAGISHI, Tatsuya; KAWAMURA, Kiyoshi; MORITA, Mikio; WO2013/161308; (2013); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem