Day: February 22, 2021

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. 22536-61-4, name is 2-Chloro-5-methylpyrimidine. A new synthetic method of this compound is introduced below., Recommanded Product: 22536-61-4

5-Methyl-2-vinylpyrimidine, Example 28.1 A 3 L 3-necked round bottomed flask was fitted with a reflux condenser, a temperature controller and a septum and was charged with 2-chloro-5-methylpyrimidine (81 mL, 778 mmol), potassium vinyltrifluoroborate (156 g, 1167 mmol), triphenylphosphine (18.02 mL, 78 mmol), cesium carbonate (156 mL, 1945 mmol) and a large stir bar. Water (1565 mL) was added, and the mixture was stirred for several min and then THF (244 mL) was added. Argon was bubbled through the mixture for 5 min and then palladium (II) chloride (1.72 g, 38.9 mmol) was added. The reaction was further sparged with argon for 5 mins. The temperature was raised to 62¡ã C. and stirring continued to completion. The reaction was then cooled to RT and filtered through two Whatman GF/F filter cups, rinsing with ether. The mixture was transferred to a separatory funnel, and the layers were separated. The aqueous layer was further extracted with diethyl ether (4*200 mL). The organic layers were combined and dried over anhydrous MgSO4 and then filtered. The mixture was partially concentrated on a rotary evaporator at 20¡ã C. and 115 torr for an extended period of time to give an orange liquid. The material was further purified by Kugel Rohr distillation to isolate the title compound (65.4 g, 70percent) as a light yellow oil. 1H NMR (400 MHz, CDCl3) delta 2.31 (s, 3H), 5.68 (d, J=10.56 Hz, 1H), 6.55 (d, J=17.22 Hz, 1H), 6.86 (dd, J=17.41, 10.56 Hz, 1H), 8.54 (s, 2H). LCMS-ESI (pos) m/z:121.1 (M+H)+.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it, 22536-61-4, 2-Chloro-5-methylpyrimidine.

Reference:
Patent; AMGEN INC.; CHEN, Xiaoqi; CHEN, Yinhong; CHENG, Alan C.; CONNORS, Richard V.; DEBENEDETTO, Mikkel V.; DRANSFIELD, Paul John; FU, Zice; HARVEY, James S.; HEATH, Julie Anne; HEDLEY, Simon J.; HOUZE, Jonathan; JUDD, Ted C.; KHAKOO, Aarif Yusuf; KOPECKY, David John; LAI, Su-Jen; MA, Zhihua; NISHIMURA, Nobuko; OLSON, Steven H.; PATTAROPONG, Vatee; SWAMINATH, Gayathri; WANG, Xiaodong; YEH, Wen-Chen; (415 pag.)US2017/320860; (2017); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 175791-49-8, The major producers of chemicals have been the Europe, Japan and China. Due to the growing call for a cleaner, greener environment, people will have to find innovative ways to maintain their relevance. Here is a compound 175791-49-8, name is 5-Bromo-7H-pyrrolo[2,3-d]pyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

To a stirred solution of 5-bromo-7H-pyrrolo[2,3-d]pyrimidine (12.8 g, 55.11 mmol) in THF was added NaH (4.48 g, 112.01 mmol) portion wise at 0C. under nitrogen. The resulting mixture was stirred at 5 C. for 1 hour then p-toluenesulfonyl chloride (11.6 g, 60.85 mmol) was added portion wise. The reaction mixture was allowed to warm to 20 C. and stirred for 3 hours. The reaction mixture was poured into a mixture of ice and 1M aq. HCl while stirring. The mixture was extracted with ethyl acetate. The combined organic layers were washed with brine, dried over MgSO4, the solids were removed by filtration and the filtrate was concentrated under reduced pressure. The residue was purified by crystallization from ethyl acetate to afford 2, 5-bromo-7-tosyl-7H-pyrrolo[2,3-d]pyrimidine as white solid. 1H NMR (400 MHz, DMSO-d6) delta ppm 2.36 (s, 3H), 7.47 (d, J=8.0 Hz, 2H), 8.06 (d, J=8.0 Hz, 2H), 8.31 (s, 1H), 9.03 (s, 1H), 9.06 (s, 1H). LC-MS ES+ m/z=351.8; Rt: 1.16 min, method D.

While traditionally a conservative industry, chemical producers will need to modernize their PR strategies to stay relevant.we look forward to future research findings about 175791-49-8, 5-Bromo-7H-pyrrolo[2,3-d]pyrimidine.

Reference:
Patent; Janssen Sciences Ireland UC; JONCKERS, Tim Hugo Maria; MC GOWAN, David Craig; RABOISSON, Pierre Jean-Marie Bernard; EMBRECHTS, Werner Constant Johan; GUILLEMONT, Jerome Emile Georges; (42 pag.)US2017/253600; (2017); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 7627-44-3, Adding some certain compound to certain chemical reactions, such as: 7627-44-3, name is 2,4-Dichloro-5-(iodomethyl)pyrimidine,molecular formula is C5H3Cl2IN2, 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 7627-44-3.

To a stirred suspension of K2CO3 (539.0 mg, 3.9 mmol) and INT-53 (750 mg, 2.6 mmol) in CH3CN (25.0 mL) was added 4-(2-methoxyethoxy)piperidine hydrochloride (250.0 mg, 1.3 mmol) at 0¡ã C. The resulting reaction mixture was stirred at room temperature for 2 h. After completion, the reaction mixture was filtered through a pad of Celite? and the filtrate was concentrated under reduced pressure. The crude material obtained was purified by column chromatography to afford INT-99 (152.0 mg, 36.5percent) as a colorless liquid. 1H NMR (400 MHz, CDCl3) delta 8.66 (s, 1H), 3.62-3.53 (m, 6H), 3.45-3.37 (m, 4H), 2.85-2.72 (m, 2H), 2.35-2.22 (m, 2H), 2.00-1.82 (m, 2H), 1.72-1.55 (m, 2H). MS m/z (M+H): 320.1.

According to the analysis of related databases, 7627-44-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Celgene Avilomics Research, Inc.; Alexander, Matthew David; Chuaqui, Claudio; Malona, John; McDonald, Joseph John; Ni, Yike; Niu, Deqiang; Petter, Russell C.; Singh, Juswinder; (164 pag.)US2016/75720; (2016); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

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. 38275-56-8, name is 5-Chloropyrimidine-2-carbonitrile. A new synthetic method of this compound is introduced below., Recommanded Product: 38275-56-8

Embodiment 10 2-cyano-5-((4,4-dimethylthiochroman-6-yl)ethynyl)pyrimidine Commercially available 4,4-dimethyl-6-ethynylthiochroman (202.8mg, 1.0mmol) and 2-cyano-5-chloropyrimidine (93mg, 0.67mmol) used as raw material were added to a flask, followed by addition of Pd(PPh3)2Cl2 (23mg, 0.03mmol) and CuI (19mg, 0.1mmol). After the flask was purged with argon for 3 times to remove oxygen, 2mL dry DMF and 0.25mL dry Et3N were added via syringe. The reaction was continued at 50C for 22 h and monitored by TLC. After completion of the reaction, the reaction solution was cooled to room temperature and the reaction was quenched with saturated ammonium chloride solution. The mixture was diluted with ethyl acetate, washed with saturated ammonium chloride solution and saturated sodium chloride solution. The organic phase was dried over anhydrous sodium sulfate, filtered, concentrated and purified by flash column chromatography (PE:EtOAc = 30:1) to give WYC-202 (133mg, 65%). 1H NMR (400 MHz, CDCl3) delta 8.89 (s, 2H), 7.55 (d, J = 1.6 Hz, 1H), 7.21 (dd, J = 8.2, 1.7 Hz, 1H), 7.11 (d, J = 8.2 Hz, 1H), 3.11 – 3.03 (m, 2H), 2.01 – 1.93 (m, 2H), 1.35 (s, 6H); 13C NMR (126 MHz, CDCl3) delta 159.21, 142.59, 141.79, 136.33, 130.15, 129.31, 126.98, 122.88, 116.13, 115.70, 101.85, 81.24, 37.02, 33.15, 30.02, 23.42. ESI(+)-MS: 306.3 [M+1]+.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it, 38275-56-8, 5-Chloropyrimidine-2-carbonitrile.

Reference:
Patent; Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences; Huazhong University of Science and Technology; CAO, Xin; YU, Biao; WANG, Ning; CHEN, Junwei; (88 pag.)EP3428155; (2019); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 13036-57-2, Adding some certain compound to certain chemical reactions, such as: 13036-57-2, name is 2-Chloro-4-methylpyrimidine,molecular formula is C5H5ClN2, 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 13036-57-2.

To a solution of methyl 3-(2,6-difluorophenylsulfonamido)-2-fluorobenzoate (6.6 g, 19.11 mmol) in tetrahydrofuran (THF) (80 mL) stirred under nitrogen at -30 C. was added the solution of LiHMDS (65 mL, 65 mmol) in tetrahydrofuran dropwise over 40 mins. The reaction mixture was stirred at -5 C. for 2 hours. The reaction mixture was cooled again to -30 C. 2-Chloro-4-methylpyrimidine (2.95 g, 22.94 mmol) in tetrahydrofuran (THF) (10 mL) was added dropwise to the reaction mixture. The reaction mixture was stirred at -10 C. for 1 h, and warmed to room temperature for another 1.5 hours. The reaction mixture was cooled to 0 C. and quenched by addition of the satureated aqueous NH4Cl(80 mL) and extracted with ethyl acetate (100 ml*3). The combined organic layers were washed with water and brine, dried over Na2SO4, filtered and concentrated under reduced pressure to afford the crude product, which was purified by silica gel chromatography with petroleum ether/EtOAc (2:1) to produce the N-(3-(2-(2-chloropyrimidin-4-yl)acetyl)-2-fluorophenyl)-2,6-difluorobenzenesulfonamide (5.05 g, 6.37 mmol, 33.3% yield). LCMS [M+H]+=442.

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. 13036-57-2, 2-Chloro-4-methylpyrimidine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Adams, Jerry Leroy; Dhanak, Dashyant; Heerding, Dirk A.; Manning, Calvin O.; US2013/53562; (2013); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

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. 23002-51-9, name is 6-Chloro-1H-pyrazolo[3,4-d]pyrimidine, molecular formula is C5H3ClN4, The 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. Quality Control of 6-Chloro-1H-pyrazolo[3,4-d]pyrimidine

Example 74 : N-( 1 -Methyl- 1 H-pyrazo 1-4-yl)- 1 -phenyl- 1 H-pyrazo lo [3 ,4-d]pyrimidin-6-amine Step (i)A suspension of 6-chloro-lH-pyrazolo[3,4-d]pyrimidine (lOOmg, 0.65mmol), benzene boronic acid (1.5eq), copper acetate (2eq) and pyridine (2eq) in dichloromethane (2mL) was heated in the microwave at 80C for 15min. After cooling to rt, the mixture was filtered and the resulting filtrate concentrated to give 6-chloro-1-phenyl-1H-pyrazolo[3,4-d]pyrimidine as a green oil (138mg, 92%) which was used without further purification in the next step.

With the rapid development of chemical substances, we look forward to future research findings about 23002-51-9.

Reference:
Patent; CELLZOME LIMITED; RAMSDEN, Nigel; HARRISON, Richard John; OXENFORD, Sally; BELL, Kathryn; PITON, Nelly; DAGOSTIN, Claudio; BOUSSARD, Cyrille; RATCLIFFE, Andrew; WO2011/48082; (2011); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 58536-46-2, The major producers of chemicals have been the Europe, Japan and China. Due to the growing call for a cleaner, greener environment, people will have to find innovative ways to maintain their relevance. Here is a compound 58536-46-2, name is 4-(4-Bromophenyl)-2,6-diphenylpyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

wherein the fluoro compound in the atmosphere of nitrogen 13H-fluorenone[1,9-ab]carbazole (15.0g, 0.52mol), 4-(4-bromophenyl)-2,6-diphenyl-pyrimidine (19.03g , 0.57mol) and then completely dissolved in 240ml xylene and sodium tert- butoxide (5.94g, added 0.61mol), and bis(tri-tert-butylphosphine)palladium (0) (0.13g, 0.0026mol, insert a) after heating and stirring for 5 hours. After concentrated under reduced pressure the xylene in the filtrate cooled to room temperature, remove the base and recrystallized from ethyl acetate to the compound 1-17: to produce a (16.31g, yield 73%).

According to the analysis of related databases, 58536-46-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; LG Chemical Co., Ltd.; Cha, Yong Bum; Kim, Jin Ju; (89 pag.)KR2016/29670; (2016); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 4994-86-9 ,Some common heterocyclic compound, 4994-86-9, molecular formula is C5H5ClN2, 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.

EXAMPLE 1 4-Chloro-2-methylpyrimidine (135 mg) was added to a solution of 1-(4-bromophenylsulphonyl)-4-(4-piperidylcarbonyl)piperazine (415 mg) in THF (15 ml) containing triethylamine (0.2 ml). The mixture was heated under reflux for 16 hours. After cooling, the THF was evaporated. The residue was treated with H2 O(20 ml) and the aqueous extracted with ethyl acetate (3*20 ml). The combined organic phases were washed with saturated brine (1*20 ml) dried and evaporated to give an oil which was purified by chromatography on silica gel. Elution with dichloromethane/methanol/0.88 NH3 (96:3:1) gave an oil. Trituration with diethyl ether (10 ml) gave, as a colourless solid, l-(4-bromophenylsulphonyl)-4-[1-(2-methylpyrimidyl)-4-piperidylcarbonyl]piperazine (152 mg), mp 200-202 C.; NMR: 1.39-1.48 (m, 2H), 1.55-1.69 (m, 2H), 2.30 (s, 3H), 2.80-3.00 (m, 7H), 3.45-3.67 (m, 4H), 4.32 (m, 2H), 6.57 (d, 1H), 7.65 (d, 2H), 7.83 (d, 2H), 8.03 (d, 1H); EI-MS m/z 508 (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,4994-86-9, its application will become more common.

Reference:
Patent; Zeneca Limited; US6093718; (2000); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 22536-65-8, With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.22536-65-8, name is 2-Chloro-5-methoxypyrimidine, molecular formula is C5H5ClN2O, molecular weight is 144.56, as common compound, the synthetic route is as follows.

A solution of (R)-4-((2-fluoro-4-piperidin-4-ylmethoxy)phenyl)-2H-benzo[ d] [1.3]oxathiole 3- oxide (150 mg, 0.41 mmol)), 2-chloro-5-methoxypyrimidine (72 mg, 0.49 mmol) and triethylamine (63 mg, 0.60 mmol) in acetonitrile (20 mL) was stirred at reflux for 6 hours. Upon cooling, a precipitate was formed, filtered off and washed sequentially with water and with hexanes. The crude product after washing was subjected to column chromatography eluting with dichloromethane to obtain the title compound (58 mg, 30 percent) as a white solid.

Statistics shows that 22536-65-8 is playing an increasingly important role. we look forward to future research findings about 2-Chloro-5-methoxypyrimidine.

Reference:
Patent; Peu Lama Na Perm Syutikeolseu In Keu .; Man Su-reu-ta-rek-su-ha-il; Cha Pi-beu-mi-ka-il; Yu Din-mi-ka-il; Ge Jen-cheu-be-i-yu-ri; Ni Ki-tin-al-rek-san-deu-reu; (190 pag.)KR2019/15535; (2019); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 1558-17-4, 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. 1558-17-4, name is 4,6-Dimethylpyrimidine, molecular formula is C6H8N2, The 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.

n-Butyllithium (2.5 M in hexanes; 5.00 mL, 12.5 mmol) was slowly added drop- wise to a -78 C solution of 4,6-dimethylpyrimidine (1.08 g, 9.99 mmol) in tetrahydrofuran (20 mL). After the reaction mixture had been stirred for 20 minutes at-78 C, solid carbon dioxide (dry ice, 5.0 g) was added, and the reaction mixture was warmed to room temperature (15 C) and stirred for 1 hour. Water (3.0 mL) was thenadded, and the resulting mixture was concentrated in vacuo to provide the product as a white solid. Yield: 1.53 g, 9.68 mmol, 97%. H NMR (400 MHz, D20) 8.78 (5, 1 H), 7.28 (5, 1 H), [3.60 (5) and 3.59 (br 5), total 2H], 2.43 (5, 3H).

While traditionally a conservative industry, chemical producers will need to modernize their PR strategies to stay relevant.we look forward to future research findings about 1558-17-4, 4,6-Dimethylpyrimidine.

Reference:
Patent; PFIZER INC.; BRODNEY, Michael Aaron; CHAPPIE, Thomas Allen; CHEN, Jinshan Michael; COE, Jotham Wadsworth; COFFMAN, Karen Jean; GALATSIS, Paul; GARNSEY, Michelle Renee; HELAL, Christopher John; HENDERSON, Jaclyn Louise; KORMOS, Bethany Lyn; KURUMBAIL, Ravi G.; MARTINEZ-ALSINA, Luis Angel; PETTERSSON, Martin Youngjin; REESE, Matthew Richard; ROSE, Colin Richard; STEPAN, Antonia Friederike; VERHOEST, Patrick Robert; WAGER, Travis T.; WARMUS, Joseph Scott; ZHANG, Yuan; (193 pag.)WO2018/163066; (2018); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia