Category: 13036-57-2

Reference of 13036-57-2, 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. 13036-57-2, name is 2-Chloro-4-methylpyrimidine, molecular formula is C5H5ClN2, 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.

[0622] Synthesis of methyl 4-methylpyrimidine-2-carboxylate: [0623] To a stirred solution of 2-chloro-4-methylpyrimidine (370 mg, 2.87 mmol) in MeOH: CH3CN (4: 1, 20 mL) under argon atmosphere were added Pd(dppf)Cl2 (420 mg, 0.57 mmol) and triethyl amine (0.8 mL, 5.75 mmol) at RT; heated to 100 C and stirred for 16 h in steel bomb under CO pressure. The reaction was monitored by TLC; after completion of the reaction, the volatiles were removed in vacuo to obtain the crude. The crude was purified through silica gel column chromatography using 40% EtOAc/ Hexanes to afford methyl 4-methylpyrimidine-2-carboxylate (330 mg, 75%) as an off-white solid. [0624] 1H-NMR (CDC13, 400 MHz): delta 8.78 (d, 1H), 7.31 (d, 1H), 4.01 (s, 3H), 2.68 (s, 3H); LC-MS: 97.40%; 153.2 (M++l); (column: X Bridge C-18, 50 3.0 mm, 3.5 muiotaeta); RT 0.68 min. 5 mM NH4OAc: ACN; 0.8 mL/min); TLC: 50% EtOAc/ Hexanes (R 0.2).

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 13036-57-2, 2-Chloro-4-methylpyrimidine.

Reference:
Patent; ENVIVO PHARMACEUTICALS, INC.; RIPKA, Amy; SHAPIRO, Gideon; MCRINER, Andrew, J.; BURSAVICH, Matthew, Gregory; WO2013/142269; (2013); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 13036-57-2, 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.13036-57-2, name is 2-Chloro-4-methylpyrimidine, molecular formula is C5H5ClN2, molecular weight is 128.56, as common compound, the synthetic route is as follows.

Step E: 2-Propen-1-yl [3-[(2-chloro-4-pyrimidinyl)acetyl]-2-(methyloxy)phenyl]carbamate; To a solution of methyl 2-(methyloxy)-3-{[(2-propen-1-yloxy)carbonyl]amino}benzoate (123 g, 464 mmol,) in dry THF (800 mL) at -10 C., LiHMDS (1M in THF, 1440 mmol, 1440 mL) was added dropwise and the solution was allowed to stir for 1 h at 0 C. A solution of 2-chloro-4-methylpyrimidine (72 g, 560 mmol) in THF (150 mL) was then added dropwise to the solution of ester and base at 0 C. over 20 min. The solution was allowed to stir 1 h at rt. TLC showed the reaction was complete. The reaction was quenched by addition of the saturated aqueous NH4Cl (800 mL) at 0 C. The reaction mixture was extracted with EtOAc (1 L×3). The combined organic layers were washed with water and brine successively, dried over Na2SO4, filtered and concentrated under reduced pressure to give the crude product, which was purified by flash column on silica gel, eluting with DCM. This solution was evaporated to obtain a solid. The orange solid was triturated with a small amount of EtOAc and filtered, rinsing with diethyl ether to give the title compound of Step E (109.9 g, 67.8% yield). 1H NMR (400 MHz, CDCl3) delta ppm 13.64-13.68 (br, 1H), 8.38 (d, J=5.3 Hz, 1H), 8.15-8.21 (m, 1H), 7.31-7.39 (m, 2H), 7.15-7.18 (m, 1H), 6.87 (d, J=5.3 Hz, 1H), 6.19 (s, 1H), 5.92-6.15 (m, 1H), 5.23-5.40 (m, 2H), 4.66-4.70 (m, 2H), 3.76 (s, 3H).

The chemical industry reduces the impact on the environment during synthesis 13036-57-2, I believe this compound will play a more active role in future production and life.

Reference:
Patent; Adams, Jerry Leroy; Dickerson, Scott Howard; Johnson, Neil W.; Kuntz, Kevin; Petrov, Kimberly; Ralph, Jeffrey M.; Rheault, Tara Renae; Schaaf, Gregory; Stellwagen, John; Tian, Xinrong; Uehling, David Edward; Waterson, Alex Gregory; Wilson, Brian; US2009/298815; (2009); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 13036-57-2, 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. 13036-57-2, name is 2-Chloro-4-methylpyrimidine, molecular formula is C5H5ClN2, 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.

To a solution of 2-chloro-4-methylpyrimidine (Ig5 7.78mmol) and zinc cyanide (475mg, 4.04mmo) in anhydrous DMF (10ml) was added Pd(PPh3)4 (449mg, 0.366mmol) and nitrogen flushed through the mixture for 5 min. The mixture was heated at 180C for 30 min in a microwave reactor. The reaction was repeated on the same scale and the reaction mixtures were combined. The mixture was partitioned between EtOAc and water (filtered through celite to remove some insolubles), and the organic layer washed with sat. NaCl5 dried over MgStheta4, filtered and evaporated. The residue was purified by MPLC (Biotage Horizon; FLASH 25+M) eluent: 100% Hexanes (90ml), gradient rising from 100% Hexanes to 15% EtOAc in Hexanes (900ml), then 15% EtOAc in Hexanes (500ml) to give Ig of the title compound (54%) as an off- white solid. 1H NMR (CDCl3): 2.62 (s, 3H), 7.42 (d, J 5.1 Hz, 1H)5 8.69 (d, J 5.1 Hz, 1H).

According to the analysis of related databases, 13036-57-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK SHARP & DOHME CORP.; EDMONDSON, Scott, D.; CHANG, Lehua; KAR, Nam Fung; MORRIELLO, Gregori, J.; MOYES, Christopher, J.; SHEN, Dong-Ming; ZHU, Cheng; ANTHONY, Neville, J.; JONES, Philip; SMITH, Graham, F.; SCOTT, Mark, E.; THOMPSON, Christopher, F.; JUNG, Joon; CAMMARANO, Carolyn; HOFFMAN, Dawn Marie; WO2011/25774; (2011); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 13036-57-2 , The common heterocyclic compound, 13036-57-2, name is 2-Chloro-4-methylpyrimidine, 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.

To a solution of ethyl 3-{[(2,6-diotafluorophenyl)sulfonyl]amiotano}-4-fluorobenzoate (5 0 g, 13 9 mmol) in THF (100 mL) was added 1 0 M LHMDS in THF (34 8 mL, 34 8 mmol) A solution of 2-chloro-4-methylpyriotamiotadiotane (2 7 g, 20 9 mmol) in THF (100 mL) was added dropwise over 30 mm, and the reaction was stirred overnight at rt The reaction was quenched with 10 mL of MeOH and concentrated, and the residue was partitioned between EtOAc and saturated aqueous sodium bicarbonate The aqueous layer was extracted with 2×50 mL EtOAc, and the combined organic layers were passed through a pad of silica gel, concentrated, and adsorbed onto silica gel The crude product was purified via flash chromatography with 0-100% EtOAc/DCM to generate 3 07 g (50% yield) of the product of Step B as a white powder ES- LCMS m/z 443 (M+H)

The synthetic route of 13036-57-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXOSMITHKLINE LLC; ADJABENG, George; BAUM, Erich; BIFULCO, Neil; DAVIS-WARD, Ronda, G.; DICKERSON, Scott, Howard; DONALDSON, Kelly, Horne; HORNBERGER, Keith; PETROV, Kimberly; RHEAULT, Tara, Renae; SAMMOND, Douglas, McCord; SCHAAF, Gregory, M.; STELLWAGEN, John; UEHLING, David, Edward; WATERSON, Alex, Gregory; WO2010/104899; (2010); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 13036-57-2, 2-Chloro-4-methylpyrimidine, 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, COA of Formula: C5H5ClN2, blongs to pyrimidines compound. COA of Formula: C5H5ClN2

Example 4 [00154] The compound is prepared as follows: [00155] The synthetic route to obtain compound 4 started from a chloration of 4-methyl-2- chloropyrimidine. Compound 1 was obtained in 28% yield after purification. The SNAr reactionwas carried out in 52% yield. The Stille reaction was then realised. The product 3 was obtained in 72% yield. The introduction of piperidine was then carried out under microwave conditions. After purification, the final product was obtained in 19% yield.

The synthetic route of 13036-57-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NOGRA PHARMA LIMITED; HOMMES, Daan; VERHAAR, Auke; VAN DEN BRINK, Gijs; VITI, Francesa; WO2013/178816; (2013); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 13036-57-2 ,Some common heterocyclic compound, 13036-57-2, 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.

To a solution containing 37 g (188 mmol) of methyl 3,5-bis(methyloxy)benzoate and 300 mL of THF at 00C was added 395 mL (395 mmol) of a 1.0 M solution of LHMDS in THF. To this mixture, a solution containing 29 g (226 mmol) of 2-chloro-4- methylpyrimidine and 100 mL was added dropwise over about 30 min. The reaction mixture was allowed to stir for an additional 30 min and quenched by the addition of 100 mL of MeOH. The solvents were removed under reduced pressure and the residue was partitioned between EtOAc and water. The combined organic layers were dried over MgSO4 and filtered, washing the filter cake with copious amounts of EtOAc and DCM to dissolve precipitated product. The solvents were removed under reduced pressure and the resulting orange solid was triturated from EtOAc to give 46.5 g (85%) of 1-[3,5-bis(methyloxy)phenyl]-2-(2-chloro-4-pyrimidinyl)ethanone as a light tan solid, which exists as a mixture of ketone and enol tautomers: MS (ESI): 293.29 (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,13036-57-2, its application will become more common.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2009/32667; (2009); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 13036-57-2, 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.13036-57-2, name is 2-Chloro-4-methylpyrimidine, molecular formula is C5H5ClN2, molecular weight is 128.56, as common compound, the synthetic route is as follows.

A solution of Lithium bis(trimethylsilyl)amide (1M in THF, 10.26mL, 10.26mmol) was added to a cooled (0C) solution of Methyl 3-((tert-butoxycarbonyl)amino)-2- fluorobenzoate (790mg, 2.93mmol) in THF (15mL). After lOmin of stirring, a solution of 2-chloro-4-methylpyrimidine (452mg, 3.52mmol) in THF (2mL) was slowly added and the reaction mixture was allowed to warm to 40C for lh. Aqueous saturated ammonium chloride was added to the medium. The aqueous layer was extracted with EtOAc (2 times). Combined organics were washed with brine, dried over sodium sulphate, filtered and the filtrate was concentrated under reduced pressure. Purification of the residue by flash chromatography on silica gel (cHex-EtOAc 1/0 to 0/1) afforded the title compound (880mg, 82%). LC/MS (ES+): 366.3-368.3 (M+l).

Statistics shows that 13036-57-2 is playing an increasingly important role. we look forward to future research findings about 2-Chloro-4-methylpyrimidine.

Reference:
Patent; CELLIPSE; PRUDENT, Renaud; PAUBLANT, Fabrice; (74 pag.)WO2018/55097; (2018); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 13036-57-2, 2-Chloro-4-methylpyrimidine, 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, blongs to pyrimidines compound. Computed Properties of C5H5ClN2

Example 11, Step E[00133] A solution of compound 11f (68 mg, 0.2 mmol), 2-chloro-4-methylpyrimidine (31 mg, 0.24 mmol), Pd2(dba)3 (22.85 mg, 0.025 mmol), Xant-phos (28.9 mg, 0.05 mmol) and Cs2C03 (98 mg, 0.3 mmol) in dioxane (3 mL) was heated to reflux for 4 hrs under N2. After cooling to r.t., the mixture was diluted with H20 (10 mL) and extracted with EtOAc (10 mL*2), the combined organic layers were dried over Na2S04, concentrated in vacuo and purified by preparative TLC (EtOAc: PE = 2:1 ) to give product 11g (52.4 mg, 62%).[00134] This compound was characterized by mass spectroscopy (MS) in accordance with the procedures described herein. Mass spectroscopy indicated MS (ESI): m/z 431 (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,13036-57-2, its application will become more common.

Reference:
Patent; MERCK SHARP & DOHME CORP.; ADDEX PHARMA SA; LIVERTON, Nigel, J.; BOLEA, Christelle; CELANIRE, Sylvain; LUO, Yunfu; WO2012/6760; (2012); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products 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.

Ethyl 3-{[(2-propen-1 -yloxy)carbonyl]amino}benzoate (20.0 g, 80.24 mmol) was dissolved in 1 M LiHMDS in THF (260 mL) and cooled to 0 C. A solution containing 2-chloro-4-methylpyrimidine (10.32 g, 80.24 mmol) in 20 mL dry THF was added to the reaction mixture. The reaction was stirred at 0 C for 2 h, quenched with MeOH (100 mL), dried directly onto silica, and purified via flash chromatography EtOAc/CH2Cl2 0-100% gradient run over 60 min. The desired fractions were combined and the solvent was removed to give the title compound. 13.6 g (51 % yield) ES-LCMS m/z 332 (M+H).

According to the analysis of related databases, 13036-57-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GLAXOSMITHKLINE LLC; ADAMS, Jerry, Leroy; FAITG, Thomas; KASPAREC, Jiri; PENG, Xin; RALPH, Jeffrey; RHEAULT, Tara Renae; WATERSON, Alex Gregory; WO2011/59610; (2011); 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