Category: 74290-68-9

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

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 74290-68-9 as follows. Formula: C5H6BrN3

General procedure: 2-Bromo-3-methylpyrazine (104 mg, 0.600 mmol),tetrakis(triphenylphosphine)palladium(0) (95%, 133 mg, 0.109 mmol) and sodium carbonate(175 mg, 1.64 mmol) were combined with 4-[3-methoxy-4-(4,4,5,5-tetramethyl-1 3,2-dioxaborolan-2-yl)phenoxy]furo[3 ,2-c]pyridine [Cl 0, which was prepared in analogous fashion to4-[3-methyl-4-(4 ,4,5,5-tetramethyl-1 ,3 ,2-dioxaborolan-2-yl)phenoxy]furo[3,2-c]pyrid me (C2) inExample 1] (200 mg, 0.545 mmol) in 1,4-dioxane (3 mL) and water (1 mL). The reaction mixturewas heated to 13000 in a microwave reactor for 1 hour. The mixture was cooled to roomtemperature, and the supernatant was decanted into another flask. The remaining solids were washed with ethyl acetate (3 x 10 mL) and the combined organic portions were concentrated in vacuo. Purification was carried out twice using silica gel chromatography (First column: Eluent:2% methanol in dichloromethane; Second column: Gradient: 0% to 100% ethyl acetate inheptane). The colorless fractions were combined and concentrated under reduced pressure to provide the product as a white solid. Yield: 85 mg, 0.25 mmol, 46%. LCMS m/z 334.0 (M+H). 1H NMR (400 MHz, ODd3) oe 8.47 (AB quartet, downfield doublet is broadened, JAB=2.S Hz, AVAB=l4 Hz, 2H), 8.08 (d, J=5.9 Hz, 1H), 7.66 (d, J=2.3 Hz, 1H), 7.36 (d, J8.0 Hz, 1H), 7.25- 7.28 (m, 1H, assumed; partially obscured by solvent peak), 6.90-6.96 (m, 2H), 6.88 (dd, J=2.2,0.8 Hz, 1H), 3.79 (s, 3H), 2.50 (s, 3H). Yellow fractions were repurified to provide additional product: 55 mg, overall yield: 75%.

According to the analysis of related databases, 74290-68-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; PFIZER INC.; COE, Jotham, Wadsworth; ALLEN, John, Arthur; DAVOREN, Jennifer, Elizabeth; DOUNAY, Amy, Beth; EFREMOV, Ivan, Viktorovich; GRAY, David, Lawrence, Firman; GUILMETTE, Edward, Raymond; HARRIS, Anthony, Richard; HELAL, Christopher, John; HENDERSON, Jaclyn, Louise; MENTE, Scot, Richard; NASON, Deane, Milford, II; O’NEIL, Steven, Victor; SUBRAMANYAM, Chakrapani; XU, Wenjian; WO2014/72881; (2014); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

74290-68-9, name is 6-Bromo-5-methylpyrazin-2-amine, 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. Quality Control of 6-Bromo-5-methylpyrazin-2-amine

A mixture of compound 15a (100 g, 0.53 mol) and ClCH2CHO (500 g (400 mL), 3.20 mol, 50 wt % aqueous solution) in H2O (600 mL) was refluxed for 5 h. The reaction mixture was concentrated to remove ClCH2CHO then extracted with EtOAc (600 mL¡Á3). The combined organic layers were concentrated and recrystallized from EtOAc and petroleum ether. The mother liquor was purified by column chromatography eluted with petroleum ether/EtOAc (2:1?1:1) to give 5-bromo-6-methylimidazo[1,2-a]pyrazine 1 (50 g, 44%) as a yellow solid; mp 145-148 C; IR (KBr): 3100, 1495, 1324, 1295, 1145, 771 cm-1; 1H NMR (400 MHz, CDCl3): delta=8.99 (s, 1H), 7.87-7.84 (m, 2H), 7.69 (s, 3H); 13C NMR (100 MHz, CDCl3): delta=140.0 (2C), 139.0, 134.8, 115.0, 110.4, 22; HRMS-ESI: calcd for C7H7BrN3 (M+H)+: 211.9823 and 213.9803; found: 211.9817 and 213.9797.

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

Reference:
Article; Harris, Anthony R.; Nason, Deane M.; Collantes, Elizabeth M.; Xu, Wenjian; Chi, Yushi; Wang, Zhihan; Zhang, Bingzhi; Zhang, Qingjian; Gray, David L.; Davoren, Jennifer E.; Tetrahedron; vol. 67; 47; (2011); p. 9063 – 9066;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Related Products of 74290-68-9, 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. 74290-68-9, name is 6-Bromo-5-methylpyrazin-2-amine belongs to pyrazines compound, it is a common compound, a new synthetic route is introduced below.

6-Bromo-5-methylpyrazin-2-amine (which may be prepared according to the method ofN. Sato, J. Heterocycl. Chem. 1980, 171, 143-147) (2.40 g, 12.8 mmol), 4-[3-methyl-4-(4,4,5,5- tetramethyl- 1,3 ,2-d ioxaborolan-2-yl)phenoxy]furo[3,2-c]pyridine (C2) (4.48 g, 12.8 m mol), and tetrakis(triphenylphosphine)palladium(0) (95%, 466 mg, 0.383 mmol) were combined in a pressure tube and dissolved in 1 ,4-dioxane (60 mL) and ethanol (20 mL). A solution of sodium carbonate (2.0 M in water, 19.1 mL, 38.2 mmol) was added, and argon was bubbled through thereaction mixture for 15 minutes. The tube was sealed, and then heated at 140 00 for 16 hours. The reaction mixture was combined with a second, identical, reaction mixture for workup. The combined reaction mixtures were filtered; solids remaining in the reaction vessels were slurried in water and filtered, and the filter cake was washed with ethanol. All of the organic filtrates were passed through a pad of Celite, and the Celite pad was washed with ethanol. These filtrates were concentrated in vacuo, and the resulting solid was slurried in water, filtered and washedwith water. The solid was then slurried in 1:1 heptane I diethyl ether, filtered and washed withdiethyl ether to afford the product as a light yellow solid. Yield: 6.774 g, 20.38 mmol, 80%. 1HNMR (500 MHz, DMSO-d6) oe 8.14 (d, J=2.2 Hz, 1H), 8.01 (d, J=5.7 Hz, 1H), 7.82 (s, 1H), 7.47(dd, J=5.8, 0.9 Hz, 1H), 7.21 (d, J=8.3 Hz, 1H), 7.15 (brd, J=2.4 Hz, 1H), 7.09 (brdd, J=8.2, 2.4Hz, 1H), 7.06 (dd, J=2.2, 0.7 Hz, 1H), 6.18 (br s, 2H), 2.12 (s, 3H), 2.07 (br s, 3H).

The synthetic route of 6-Bromo-5-methylpyrazin-2-amine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PFIZER INC.; COE, Jotham, Wadsworth; ALLEN, John, Arthur; DAVOREN, Jennifer, Elizabeth; DOUNAY, Amy, Beth; EFREMOV, Ivan, Viktorovich; GRAY, David, Lawrence, Firman; GUILMETTE, Edward, Raymond; HARRIS, Anthony, Richard; HELAL, Christopher, John; HENDERSON, Jaclyn, Louise; MENTE, Scot, Richard; NASON, Deane, Milford, II; O’NEIL, Steven, Victor; SUBRAMANYAM, Chakrapani; XU, Wenjian; WO2014/72881; (2014); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem