Tag: M.W=0-100

Synthetic Route of C4H5N3. The fused heterocycle is formed by combining a benzene ring with a single heterocycle, or two or more single heterocycles. Compound: 4-Aminopyrimidine, is researched, Molecular C4H5N3, CAS is 591-54-8, about Palladium-Catalyzed Hydroxycarbonylation of (Hetero)aryl Halides for DNA-Encoded Chemical Library Synthesis. Author is Li, Jian-Yuan; Miklossy, Gabriella; Modukuri, Ram K.; Bohren, Kurt M.; Yu, Zhifeng; Palaniappan, Murugesan; Faver, John C.; Riehle, Kevin; Matzuk, Martin M.; Simmons, Nicholas.

A strategy for DNA-compatible, palladium-catalyzed hydroxycarbonylation of (hetero)aryl halides on DNA-chem. conjugates has been developed. This method generally provided the corresponding carboxylic acids in moderate to very good conversions for (hetero)aryl iodides and bromides, and in poor to moderate conversions for (hetero)aryl chlorides. These conditions were further validated by application within a DNA-encoded chem. library synthesis and subsequent discovery of enriched features from the library in selection experiments against two protein targets.

Here is a brief introduction to this compound(591-54-8)Synthetic Route of C4H5N3, if you want to know about other compounds related to this compound(591-54-8), you can read my other articles.

Reference:
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Huang, Pan; Le, Xiangyang; Huang, Fei; Yang, Jie; Yang, Haofeng; Ma, Junlong; Hu, Gaoyun; Li, Qianbin; Chen, Zhuo published an article about the compound: 4-Aminopyrimidine( cas:591-54-8,SMILESS:C1=CN=CN=C1N ).Name: 4-Aminopyrimidine. Aromatic heterocyclic compounds can be classified according to the number of heteroatoms or the size of the ring. The authors also want to convey more information about this compound (cas:591-54-8) through the article.

Apcin is one of the few compounds that have been previously reported as a Cdc20 specific inhibitor, although Cdc20 is a very promising drug target. We reported here the design, synthesis, and biol. evaluations of 2,2,2-trichloro-1-aryl carbamate derivatives as Cdc20 inhibitors. Among these derivatives, compound 9f(I) was much more efficient than the pos. compound apcin in inhibiting cancer cell growth, but it had approx. the same binding affinity with apcin in SPR assays. It is possible that another mechanism of action might exist. Further evidence demonstrated that compound 9f also inhibited tubulin polymerization, disorganized the microtubule network, and blocked the cell cycle at the M phase with changes in the expression of cyclins. Thus, it induced apoptosis through the activation of caspase-3 and PARP. In addition, compound 9f inhibited cell migration and invasion in a concentration-dependent manner. These results provide guidance for developing the current series as potential new anticancer therapeutics.

Here is a brief introduction to this compound(591-54-8)Name: 4-Aminopyrimidine, if you want to know about other compounds related to this compound(591-54-8), you can read my other articles.

Reference:
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 5049-61-6, These common heterocyclic compound, 5049-61-6, name is Pyrazin-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.

General procedure: In a stainless reactor bomb, the respective aromatic amine (1.0mmol), 4c (0.50 mol%), K2CO3 (5.0 mol%), and MeOH (1.0 mL) were placed. Then, the reactor was sealed with a stainless stopper, and the mixture was stirred for 17 h at 120 C. After removing MeOH under reduced pressure, the products were isolated by silica gel column chromatography.

The synthetic route of 5049-61-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Toyooka, Genki; Tuji, Akiko; Fujita, Ken-Ichi; Synthesis; vol. 50; 23; (2018); p. 4617 – 4626;,
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. 109-08-0, name is 2-Methylpyrazine, A new synthetic method of this compound is introduced below., SDS of cas: 109-08-0

General procedure: A 25 mL Schlenk tube equipped with a magneticstirring bar was charged with2,6-lutidine (0.75 mmol, 3equiv.), p-nitro-benzaldehyde(0.25 mmol), dioxane/water(1:1, 1ml) and [Hmim][H2PO4](1equiv.).The tube was sealed and heated at 100 for 24h. Aftercompletion of the reaction, the resulting solution was extracted with ether (3×10 ml). The organic layer was dried with anhydrous Na2SO4,and concentrated under vacuum. The residue was chromatographed on a silica gelcolumn eluted with a mixture of petroleum ether and ethyl acetate (1:1) to givepure products (92percent).

The synthetic route of 109-08-0 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Zhang, Xue-Yan; Dong, Dao-Qing; Yue, Tao; Hao, Shuang-Hong; Wang, Zu-Li; Tetrahedron Letters; vol. 55; 40; (2014); p. 5462 – 5464;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 109-08-0, A common heterocyclic compound, 109-08-0, name is 2-Methylpyrazine, molecular formula is C5H6N2, 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.

In the glove box, Mn(CO)5Br (0.005mmol), [(E)-2-(2-(1-(2-pyridine)ethylidene)-indenyl)pyridine] (0.006 mmol),After adding 1.0 mL of toluene and stirring for two hours, 2-methylpyrazine 1a (2 mmol) was added.Benzyl alcohol 2e (1 mmol), after reacting at 135 ° C for 48 hours, the reaction was stopped, and the solvent was evaporated to dryness.Column chromatography ethyl acetate / petroleum ether (1:10),Trans-disubstituted olefin derivative 3e. The product was a white solid with a yield of 83percent.

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; Qingdao University of Science and Technology; Zhang Chunyan; (19 pag.)CN108250153; (2018); A;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 4949-13-7, The chemical industry reduces the impact on the environment during synthesis 4949-13-7, name is 2-Fluoropyrazine, I believe this compound will play a more active role in future production and life.

General procedure: To a 5 mL vial containing a stir bar, 3-(2-aminopyrimidin-5-yl)-6-cyclobutyl-2-fluorophenol (80 mg, 0.31 mmol) and 2-chloropyrimidine (41 mg, 0.34 mmol) were added Cs2CO3 (203 mg, 0.62 mmol) and DMSO (0.8 mL). The resultant mixture was stirred at 120 Celsius for approximately 1 hour via microwave irradiation. The reaction mixture was cooled to room temperature before passing the mixture through a syringe filter and subjecting the filtrate to FCC to afford the title compound (81 mg, 78%). The title compound was prepared using conditions similar to those described in Example 160 with DMSO as the solvent, heating for 2 hours at 80 Celsius via microwave radiation and substituting Intermediate B and 2-fluoropyrazine. MS (ESI): mass calcd. for C18H16FN6O, 337.13; m/z found, 337.9 [M+H]+. 1H NMR (400 MHz, CDCl3) delta 8.53 (d, J=1.3 Hz, 1H), 8.49-8.42 (m, 1H), 8.27 (d, J=2.7 Hz, 1H), 8.12-8.03 (m, 2H), 7.85-7.76 (m, 1H), 7.23 (s, 1H), 4.70 (s, 2H), 3.68-3.56 (m, 1H), 2.26-2.08 (m, 4H), 2.03-1.89 (m, 1H), 1.87-1.76 (m, 1H).

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-Fluoropyrazine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; Eccles, Wendy; Fitzgerald, Anne E.; Hack, Michael D.; Hawryluk, Natalie A.; Jones, William M.; Keith, John M.; Krawczuk, Paul; Lebsack, Alec D.; Liu, Jing; Mani, Neelakandha S.; McClure, Kelly J.; Meduna, Steven P.; Rosen, Mark D.; US2014/221310; (2014); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Related Products of 5049-61-6, These common heterocyclic compound, 5049-61-6, name is Pyrazin-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.

To a solution of 2-aminopyrazine (i) (2 g, 21.02 mmol) in dry DCM (10 ml) was added NBS (3.78 g, 21.23 mmol) portion-wise under cold condition and the resulting mixture was allowed to stir at RT for 6h. 5 ml of water was added and the layers were separated. Aqueous layer was extracted with DCM (10 ml X 2). Combined organic layers were washed with Brine solution (5 ml), dried over anhydrous Na2S04 and concentrated under vacuum. Crude material was purified by column chromatography over silica gel 230-400 mesh by using 18% of ethyl acetate in petroleum ether as an eluent to afford compound (ii) (1.98 g, 54.42%) as white solid.

The synthetic route of 5049-61-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; UNIVERSITY OF CAPE TOWN; MMV MEDICINES FOR MALARIA VENTURE; YOUNIS, Yassir; CHIBALE, Kelly; WITTY, Michael, John; WATERSON, David; WO2013/121387; (2013); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Some common heterocyclic compound, 5049-61-6, name is Pyrazin-2-amine, molecular formula is C4H5N3, 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. Formula: C4H5N3

To a solution of pyrazin-2-amine(A70, 2.0 g, 2.10 mmol) and ethyl 3- bromo-2-oxopropanoate(A15, 3.0 mL, 2.30 mmol) in ethanol(15.0 mL) was added Cone., HC1(1.0 mL) at 0 C and stirred for 12 h at 95 C. The reaction mixture was concentrated under reduced pressure followed by addition of water(10 mL), the mixture was then extracted with DCM and the organic layer was washed with saturated NaHC03 solution and brine, dried over sodium sulphate, filtered and concentrated under reduced pressure. The obtained crude was purified by combi-flash purifier with 3% methanol in dichloromethane as eluent to afford the desired product A71 as yellow solid(0.4 g, 10 %). 1H NMR (DMSO-d6, 400 MHz) d 1.31(t, / = 7.2 Hz, 3H), 4.33(q, / = 7.2 Hz, 2H), 7.96(d, J = 4.4 Hz, 1H), 8.57(d, J = 4.0 Hz, 1H), 8.66(s, 1H), 9.15(s, 1H); MS(ESI) m/z = 192.1(M+H)+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5049-61-6, its application will become more common.

Reference:
Patent; JUBILANT BIOSYS LIMITED; VADIVELU, Saravanan; RAJAGOPAL, Sridharan; BURRI, Raghunadha Reddy; GARAPATY, Shivani; SIVANANDHAN, Dhanalakshmi; THAKUR, Manish Kumar; NATARAJAN, Tamizharasan; SWAMY, Indu N; NAGARAJU, Nagendra; KANAGARAJ, Subramaniam; MOHD, Zainuddin; SARKAR, Sayantani; SAMANTA, Swapan Kumar; ., Hariprakash; (284 pag.)WO2019/102494; (2019); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 4949-13-7, A common heterocyclic compound, 4949-13-7, name is 2-Fluoropyrazine, molecular formula is C4H3FN2, 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.

10264] To a 2.5 M solution of n-butyllithium (40 mE, 0.1 mol) in anhydrous THF (250 mE) cooled to -78 C. under N2 protection was added TMP (2,2,6,6-tetramethylpiperidine, 15 g, 0.106 mol) dropwise over a period of 20 minutes. The mixture was warmed to 0 C. by replacing the dry ice/acetone bath with an ice bath and stirred for 1.5 h. The mixture was cooled back to -78C. and a solution of 9a (3 g, 0.03 mol) and tributyltin chloride (10 g, 0.03 mol) in SOmE of dry THF was added over 10 mm. The mixture was stirred at -78 C. for 6 h, then warmed to -40 C. by replacing the dry ice/acetone bath with an dry ice/acetonitrile bath. A solution of 35% HC1, ethanol and THF (1:4:5) was added. The mixture was warmed to room temperature and washed with saturated NaHCO3 solution (100 mE) and extracted with EtOAc (3×100 mE). The combined organic layers were dried over anhydrous Na2504 and concentrated under reduced pressure. The residue was purified by column chromatography (silica, EtOAc:petroleum ether=1:15) to provide 9b (3.4 g, 29% yield) as light yellow oil. ?H-NMR (CDC13, 300 MHz): oe=8.41 (d, 1H), 8.17 (d, 1H), 1.8-0.53 (m, 27H).

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; Helsinn Healthcare SA; Giuliano, Claudio; Garcia Rubio, Silvina; Daina, Antoine; Guainazzi, Angelo; Pietra, Claudio; US2015/252021; (2015); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

5049-61-6, 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. 5049-61-6 name is Pyrazin-2-amine, 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.

Preparation of 3,5-dibromopyrazin-2-amine Intermediate BA) [0322] To a stirred solution of aminopyrazine (8.21 g, 86.4 mmol) in anhydrous methylene chloride (215 mL) cooled to 0C was added N-bromosuccinimide (32.3 g, 181 mmol) in portions over a six hour period, during which time the temperature of the reaction was kept below 0C. The resulting mixture was stored at 4C overnight, after which it was stirred vigorously and quenched with H20 (100 mL). The organic layer was separated, after which it was washed with saturated aqueous NaHC03, washed with brine, dried over MgS04, filtered, and evaporated in vacuo to yield a residue that was triturated with 20% EtOAc in hexanes to yield the title compound (10.3 g, 47%) as a yellow/brown powder. 1H NMR (CDC13, 300MHz) delta 8.02 (s, 1H), 5.05 (bs, 2H); HPLC retention time: 1.99 minutes; MS ESI (m/z): 252.0/254.0/256.2 (M+l)+, calc. 251.

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

Reference:
Patent; UNIVERSITY OF ROCHESTER; GELBARD, Harris, A.; DEWHURST, Stephen; GOODFELLOW, Val, S.; WIEMANN, Torsten; RAVULA, Satheesh, Babu; LOWETH, Colin, J.; WO2011/149950; (2011); A2;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem