Tag: M.W=200-300

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 143591-61-1 as follows. Product Details of 143591-61-1

To a solution of compound 102 (13.0 g, 55.9 mmol) in DMSO (150 mL) was added sodium methanethiolate (4.70 g, 67.08 mmol) as a DMSO solution (100 mL) at room temperature. The reaction mixture was stirred at 100 C. for 16 hours. The mixture was cooled to 25 C. and added to a brine solution (300 mL), and extracted with 10% IPA/dichloromethane (300 mL, 3×). The combined organic layer was dried over anhydrous sodium sulfate and concentrated. Purification by column chromatography (SiO2, ethyl acetate/hexanes (1:1)) afforded compound 103 as a yellow solid 10 g (70%). 1H-NMR (400 MHz, DMSO-d6 delta 8.15 (d, 1H), 7.88 (d, 1H), 7.83 (s, 1H), 2.6 (s, 3H).

According to the analysis of related databases, 143591-61-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Schering Corporation; US2007/105864; (2007); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application of 24241-18-7, These common heterocyclic compound, 24241-18-7, name is 2-Amino-3,5-dibromopyrazine, 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.

Zn dust (2 g, 30.6 mmol, 3.8 eq. ) and I2 (200 mg, 10percent of Zn) were added to a dry 100 mL two-necked round bottom flask under argon atmosphere. 12 mL of anhydrous THF and 8 mL of dry DMF were successively added using a syringe. The mixture was stirred at RT until the brown color of I2 disappeared. Then benzylbromide(1.5 mL, 12 mmol, 1.5 eq.) was added using a syringe and the reaction mixture was stirred at 85 °C for 3 h. After insertion of Zn, the reaction mixture was cooled to RT and 2-amino-3,5-dibromopyrazine (2g, 8 mmol, 1.0 eq.) and bis(triphenylphosphine)palladium(II) chloride (220 mg, 0.31 mmol , 11 percent of pyrazine) in 18 mL of anhydrous THF and 12 mL of dry DMF were added. The reaction mixture was continuously stirred at RT for 12 h.Then the mixture was filtered by diatomite. The filtrate was poured in 50 mL of water and extracted with ethyl acetate (3*30 mL). The organic fractions were combined and dried over anhydrous sodium sulfate and then concentrated on a rotary evaporator. The resulting residue was purified by silica gel column chromatography using petroleum ether/ethyl acetate (3/1,v/v ), affording 3-benzyl-5-bromopyrazine-2-amine (5) as a yellow viscous oil (1.8 g, 84.9percent). 1H NMR (CDCl3, 300 MHz): delta 4.10 (s, 2H,CH2), 4.60 (br s, 2H, NH2),7.10-7.41 (m, 5H, Ar-H), 8.15 (s, 1H, Ar-H); ESI-MS calcd. for C11H10BrN3: 263.0, found: 264.3 (M+H+).

The synthetic route of 24241-18-7 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Yuan, Ming-Liang; Jiang, Tian-Yu; Du, Lu-Pei; Li, Min-Yong; Chinese Chemical Letters; vol. 27; 4; (2016); p. 550 – 554;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 76537-18-3, These common heterocyclic compound, 76537-18-3, name is 3-Bromo-5-chloropyrazin-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.

Intermediate C65-Chloro-3-(2-methylthiazol-5-yI)pyrazi n-2-am i ne A mixture of 2-methyl-5-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)thiazole (1 g, 4.44 mmol), 3-bromo-5-chloropyrazin-2-amine (0.926 g, 4.44 mmol), PdCI2(dppf).CH2CI2 adduct (0.181 g, 0.222 mmol) and 2 M Na2CO3 (6.66 ml) in DME (22.21 ml) under N2 was heatedusing microwave radiation at 120C for 45 mins. The mixture was added to water (100 ml) and extracted with EtOAc (2 x 90 ml). The organic extracts were washed with brine, dried over Mg504 and concentrated under reduced pressure. Purification by chromatography on silica eluting with 0-10% [2.OM NH3 in MeOH] in TBME afforded the title compound as a brown solid;LCMS: Rt 0.87 mins; MS mlz 227.1 [M+H]+; Method 2minLC_v003.

The synthetic route of 76537-18-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NOVARTIS AG; BELLENIE, Benjamin Richard; BLOOMFIELD, Graham Charles; BRUCE, Ian; CULSHAW, Andrew James; HALL, Edward Charles; HOLLINGWORTH, Gregory; NEEF, James; SPENDIFF, Matthew; WATSON, Simon James; (395 pag.)WO2015/162459; (2015); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 63744-22-9, 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. 63744-22-9 name is 6,8-Dibromoimidazo[1,2-a]pyrazine, 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 1Part A: The title compound was prepared according to US20060106023 (A1 ).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 6,8-Dibromoimidazo[1,2-a]pyrazine, and friends who are interested can also refer to it.

Reference:
Patent; SCHERING CORPORATION; ALBANY MOLECULAR RESEARCH, INC.; WO2009/97233; (2009); 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. 1458-01-1, name is Methyl 3,5-diamino-6-chloropyrazine-2-carboxylate, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 1458-01-1

Preparation 1Methyl 3,5-diamino-6-r2-(trifluoromethoxy)phenyllpyrazine-2-carboxylateMETHOD AMethyl 3,5-diamino-6-chloropyrazine~2-carboxylate (1.62 g, 8.0 mmol) was combined with 2-(trifluoromethyl)phenylboronic acid (3.29 g: 16.0 mmol), palladium tetrakistriphenylphosphine (0.924 g, 0.80 mmol) and cesium carbonate (2.61 g, 8.0 mmol) and suspended in a mixture of 1 ,4-dioxane (30 ml) and water (15 ml). The reaction was sealed and heated to 750C for 4 hours before cooling to room temperature. Water (150 ml) was added and the 1 ,4-dioxane removed in vacuo. The precipitate formed was collected by filtration and dried. The brown solid was triturated with dichloromethane:methanol, then purified by silica gel column chromatography eluting with 95:5 dichloromethane:methanol to afford the title compound as a yellow solid (1.66 g, 63percent yield).1HNMR (d6-DMSO): 3.7 (s, 3H), 6.59 (br s, 2H), 7.10 (br s, 2H), 7.41-7.64 (m, 4H) LCMS Rt=8.64 min MS m/z 329 [MH]+

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 1458-01-1.

Reference:
Patent; PFIZER LIMITED; WO2008/135830; (2008); 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. 24241-18-7, name is 2-Amino-3,5-dibromopyrazine, A new synthetic method of this compound is introduced below., Product Details of 24241-18-7

Example 54; Step 1; A suspension of 1 (3 g, 11.64 mmol) in 25% aq. NH4OH (15 mL) in sealed tube was heated at 110 C. for 16 h. After completion of reaction (reaction progress was monitored by TLC), the reaction mixture was partitioned between ethyl acetate-water (3×50 mL). The combined extracts were washed with saturated brine, dried and evaporated under reduced pressure. The residue was purified by column chromatography on silica gel eluted with 15% ethyl acetate-hexane to afford 2 as a yellow solid (2.1 g, 93%). MS m/z (ES): 189 (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; de Vicente Fidalgo, Javier; Hermann, Johannes Cornelius; Lemoine, Remy; Li, Hongju; Lovey, Allen John; Sjogren, Eric Brian; Soth, Michael; US2011/59118; (2011); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application of 723286-79-1,Some common heterocyclic compound, 723286-79-1, name is tert-Butyl 5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazine-7(8H)-carboxylate, molecular formula is C10H16N4O2, 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 solution of 9.01 g (40.0 mmol) of 7- (tert-butoxycarbonyl)-5, 6,7, 8- tetrahydro [1, 2,4] triazolo [4, 3-a] pyrazine in 150 mL chloroform was added 6.72 g (80.0 mmol) of sodium bicarbonate. The system was cooled to 0 C and 7.11 g (40.0 mmol) OF N- bromosuccinimide was added. The reaction was stirred at 0 C for 15 min and at ambient temperature for 16 h. The reaction was diluted with dichloromethane and washed sequentially with saturated aqueous sodium bicarbonate solution and brine, dried over magnesium sulfate, and concentrated in vacuo. The crude product was purified by flash chromatography on a BIOTAGE system (silica gel, 4% methanol/ethyl acetate) to yield the title compound. LC/MS 303.0 and 305.0 (M+1).

The synthetic route of 723286-79-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK & CO., INC.; WO2004/58266; (2004); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 24241-18-7, 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 24241-18-7 as follows.

Intermediate Example 1 – 1 : Preparation of 6,8-dibromo-imidazo[ 1 , 2-a]pyrazineTo a stirred suspension of 2-amino-3, 5-dibrompyrazine (427 g, 1688mmol) in water (6.4 L) / THF (482 mL), at rt was added bromacetaldehyde-diethylacetal (998 g, 5065 mmol) in one portion. After stirring under reflux for 4 h, the clear orange solution was stirred for an additional 15 h at rt. The suspension was filtered, and the remaining solid was washed with MeOH (2 L) and dried in vaccuo at 60 C to yield 6,8-dibromo-imidazo[1 ,2-a]pyrazine as an off-white solid (500 g, 107% with residual MeOH) : 1 H-NM (300 MHz, d6-DMSO): delta =9.02 (s, 1 H), 8.23 (d, 1 H), 7.89 (d, 1 H) ppm. UPLC-MS: RT = 0.80 min; m/z 277.9 [MH+]; required MW = 276.9.

According to the analysis of related databases, 24241-18-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; KOPPITZ, Marcus; KLAR, Ulrich; JAUTELAT, Rolf; KOSEMUND, Dirk; BOHLMANN, Rolf; BADER, Benjamin; LIENAU, Philip; SIEMEISTER, Gerhard; WO2012/80228; (2012); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 446286-94-8, 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. 446286-94-8, name is 5-Bromo-N,N-dimethylpyrazin-2-amine belongs to pyrazines compound, it is a common compound, a new synthetic route is introduced below.

To asolution of dimethyl amino 3d (1370 mg, 6.82mmol) in drytetrahydrofuran (50 mL) under Ar at 80 C was slowly added1.57M n-butyllithium hydride (n-BuLi) in hexane (10.8 mL).After stirring for 60min at 80 C, to the mixture was addedN,N-dimethylformamide (DMF) (2.0 mL, 26mmol) and theresulting solution was allowed to warm to r.t. After stirring for1 h, to the reaction mixture was added water to decompose theexcess reducing agent. Further, to the mixed solution was addedwater followed by extraction with ethyl acetate (3 200 mL).The combined organic layers were dried over Na2SO4, filtered,and the solvents were removed under reduced pressure. Theresidue obtained was purified by silica gel column chromatography(hexane/ethyl acetate = 1/1) to yield arylaldehyde 4d (975 mg, 6.46mmol, 95%) as a light yellow solid: mp 112 C;IR (neat, , cm1): 2783, 1681, 1373, 1008; 1HNMR (500MHz, CDCl3) 9.91 (s, 1H), 8.69 (s, 1H), 8.08 (d, J = 1.1 Hz,1H), 3.26 (s, 6H); 13CNMR (126 MHz, CDCl3) 190.7, 155.5,144.3, 136.8, 129.4, 37.9; HR-ESI-MS: m/z: [M+ H]+ calculatedfor C7H10N3O, 152.0824; found, 152.0814.

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, 5-Bromo-N,N-dimethylpyrazin-2-amine, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Saito, Ryohei; Kuchimaru, Takahiro; Higashi, Shoko; Lu, Shijia W.; Kiyama, Masahiro; Iwano, Satoshi; Obata, Rika; Hirano, Takashi; Kizaka-Kondoh, Shinae; Maki, Shojiro A.; Bulletin of the Chemical Society of Japan; vol. 92; 3; (2019); p. 608 – 618;,
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. 486424-37-7, name is 3-Amino-6-bromopyrazine-2-carboxylic acid, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 486424-37-7

Triethylamine (0.48 mL, 3.44 mmol) was added to a mixture of 3-amino-6-bromo-2- pyrazinecarboxylic acid (0.25 g, 1.15 mmol; described in: Ellingson, R. C.; Henry, R. L. J. Am. Chem. Soc. 1949,2798-2800), 0- (BENZOTRIAZOL-1-YL)-NNN’, N’-TETRAMETHYLURONIUM tetrafluoroborate (0.405 g, 1.26 mmol) and 1-HYDROXYBENZOTRIAZOLE (0.17 g, 1.26 mmol) in N,N-dimethylformamide/acetonitrile, (1: 1, 5ML). After stirring for 0.5 h at room temperature, 3-methoxyaniline (0.15 ML, 1. 38 mmol) was added and the resulting mixture was stirred overnight at room temperature. Water (5-10 mL) was added and the precipitate was filtered off and washed with water to give 0.25 g (68% yield) of a yellow solid: MS (ESP) m/z 323,325 (M++1).

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 486424-37-7.

Reference:
Patent; ASTRAZENECA AB; WO2004/55006; (2004); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem