Category: 4994-86-9

Synthetic Route 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.

In a microwave tube 4-chloro-2-methylpyrimidine (50 mg, 0.3 89 mmol), 6- bromo-3-fluoro-2-methylpyridine (73.9 mg, 0.389 mmol), 1,1,1,2,2,2- hexamethyldistannane (127 mg, 0.389 mmol) and Pd(Ph3P)4 (22.47 mg, 0.019 mmol)were taken in DMF (4 mL). The reaction mixture was purged with nitrogen and heated at 160 C under microwave for 1 h. The reaction mixture was concentrated, diluted with brine and ethyl acetate. The organic layer was separated, dried over Na2SO4, filtered, and concentrated which afforded brownish oil. The crude product was purified by silica gel chromatography (20-40% ethyl acetate-hexane) to afford 4-(5-fluoro-6-methylpyridin-2-yl)-2-methylpyrimidine (72 mg, 0.354 mmol, 91% yield). LCMS (ESI) m/e 204.5 [(M+H), calcd for C11H11FN3 204.11; LC/MS retention time (method B): tR = 0.75 mm.

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; BRISTOL-MYERS SQUIBB COMPANY; BRONSON, Joanne J.; CHEN, Ling; DITTA, Jonathan L.; DZIERBA, Carolyn Diane; JALAGAM, Prasada Rao; LUO, Guanglin; MACOR, John E.; MAISHAL, Tarun Kumar; NARA, Susheel Jethanand; RAJAMANI, Ramkumar; SISTLA, Ramesh Kumar; THANGAVEL, Soodamani; (318 pag.)WO2017/59080; (2017); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 4994-86-9 , The common heterocyclic compound, 4994-86-9, name is 4-Chloro-2-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 stirred solution of 4-chloro-2-methylpyrimidine (1 g, 7.77 mmol) in 1, 4- dioxane (30 mL) under a argon atmosphere were added diisopropyl ethyl amine (1.35 g, 10.50 mmol) and tert-butyl piperidin-4-ylcarbamate (1.7 g, 8.55 mmol) at RT. The reaction mixture was stirred at 150 C for 3 h. After consumption of the starting material (monitored by TLC), the reaction was diluted with water (50 mL) and extracted with EtOAc (2 x 50 mL). The combined organic extracts were dried over sodium sulfate, filtered and concentrated in vacuo. The crude material was purified through silica gel column chromatography using 5% MeOH: DCM to afford tert-butyl (1 -(2-methylpyrimidin-4-yl) piperidin-4-yl) carbamate (1.5 g, 66%) as an off-white solid. ?H-NMR (DMSO-d6, 500 MHz): oe 8.04-8.02 (m, 1H), 6.83- 6.82 (m, 1H), 6.61-6.60 (m, 1H), 4.27-4.25 (m, 2H), 3.51 (s, 1H), 2.96-2.91 (m, 2H), 2.33 (s, 3H), 1.77-1.74 (m, 2H), 1.37 (s, 9H), 1.28-1.22 (m, 2H); LC-MS: 293.3 (M+1); (column; XBridge C-18 (50 x 3.0 mm, 3.5 jim); RT 2.90 mm. 5 mM NH4OAc: ACN; 0.80 mL/min); TLC: 50% EtOAc:hexanes (R1: 0.2).

The synthetic route of 4994-86-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; FORUM PHARMACEUTICALS INC.; BURNETT, Duane, A.; BURSAVICH, Matthew, Gregory; MCRINER, Andrew, J.; WO2015/66696; (2015); 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. 4994-86-9, name is 4-Chloro-2-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. name: 4-Chloro-2-methylpyrimidine

A solution of 4-chloro-2-methylpyrimidine (100 mg, 0.778 mmol), hexamethylditin (129 mu, 0.622 mmol), tetrakis(triphenylphosphine)palladium (0) (44.9 mg, 0.039 mmol) and 6-bromo-3-fluoro-2-(fluoromethyl)pyridine (113 mg, 0.544 mmol) in 1,4-dioxane was purged with nitrogen and irradiated in a microwave at 120 C for 1 h. The reaction mixture was allowed to cool to room temperature and diluted with ethyl acetate (25 mL). The black suspension was filtered through diatomaceous earth (Celite) and the bed was washed with ethyl acetate (10 mL). The filtrate was concentrated under reduced pressure. The black residue was purified via silica gel chromatography (0-25% petroleum ether in ethyl acetate) to afford 4-(5- fluoro-6-(fluoromethyl)pyridin-2-yl)-2-methylpyrimidine (35 mg, 0.123 mmol, 16% yield) as a brown semi-solid. LCMS (ESI) m/e 222.9 [(M+H)+, calcd for (S)-2-amino-2,4-dimethylpentan-1-ol

With the rapid development of chemical substances, we look forward to future research findings about 4994-86-9.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; BRONSON, Joanne J.; CHEN, Ling; DITTA, Jonathan L.; DZIERBA, Carolyn Diane; JALAGAM, Prasada Rao; LUO, Guanglin; MACOR, John E.; MAISHAL, Tarun Kumar; NARA, Susheel Jethanand; RAJAMANI, Ramkumar; SISTLA, Ramesh Kumar; THANGAVEL, Soodamani; (485 pag.)WO2017/59085; (2017); 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. 4994-86-9, name is 4-Chloro-2-methylpyrimidine. A new synthetic method of this compound is introduced below., HPLC of Formula: C5H5ClN2

To a stirred solution of 4-chloro-2-methylpyrimidine (81 .1 mg, 631 pmol), and cyclopropyl(4-{[2-{[6-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yI)-1 H-benzimidazol-2-yl]amino}-6-(trifluoromethyl)pyridin-4-yl]methyl}piperazin-1 -yl)methanone (200 mg, 351 pmol) in Dioxane(1.7 mL) and water (340 p1) was added sodium carbonate (111 mg, 1.05 mmol) andPd(dppf)C12 . CHCl (42.9 mg, 52.6 pmol). The mixture was heated to reflux for 19 h.Dichloromethane was added, the mixture was filtered and, the solvent was removed invacuum. Preparative reverse phase HPLC (gradient of water and acetonitrile containing ammonia as additive) gave 20.0mg (10 % yield) of the title compound.LC-MS (Method 2): R = 1.16 mm; MS (ESipos): m/z = 537 [M+H]1H-NMR (400 MHz, CHLOROFORM-d) oe [ppm]: 0.725 (4.36), 0.951 (5.34), 1.261 (1.93), 1.284(6.51), 1.648 (2.11), 2.388 (3.45), 2.793 (3.68), 2.845 (16.00), 3.560 (7.24), 7.582 (2.62), 7.985 (1.62), 8.348 (0.99), 8.675 (3.91), 8.688 (3.75), 11.977 (2.41).

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, 4994-86-9, 4-Chloro-2-methylpyrimidine.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; SCHULZE, Volker; HEINRICH, Tobias; PRINZ, Florian; LEFRANC, Julien; SCHROeDER, Jens; MENGEL, Anne; BONE, Wilhelm; BALINT, Joszef; WENGNER, Antje; EIS, Knut; IRLBACHER, Horst; KOPPITZ, Marcus; BOeMER, Ulf; BADER, Benjamin; BRIEM, Hans; LIENAU, Philip; CHRIST, Clara; STOeCKIGT, Detlef; HILLIG, Roman; (1256 pag.)WO2017/102091; (2017); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 4994-86-9, Adding some certain compound to certain chemical reactions, such as: 4994-86-9, name is 4-Chloro-2-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 4994-86-9.

To a mixture of 4-chloro-2-methyl-pyrimidine (10.0 g, 7.8 mmol) and AIBN (5.1 g, 31.1 mmol) in CCl4 (100 mL) was added NBS (16.6 g, 93.3 mmol) at 25 C. and the mixture was stirred at 80 C. for 16 hrs. LCMS showed the reaction was completed. The reaction mixture was cooled down to room temperature, poured into H2O (150 mL) and extracted with DCM (80 mL¡Á2). The organic layers were combined and washed with brine (80 mL¡Á2), dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to give 2-(bromomethyl)-4-chloropyrimidine (1.7 g, yield 10.5%) as yellow oil. 1H NMR (400 MHz, CDCl3) delta=8.64 (d, J=5.6 Hz, 1H), 7.29 (d, J=5.2 Hz, 1H), 4.56 (s, 2H).

According to the analysis of related databases, 4994-86-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ESSA Pharma, Inc.; Zhou, Han-Jie; Virsik, Peter; (216 pag.)US2020/123117; (2020); A1;,
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

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. 4994-86-9, name is 4-Chloro-2-methylpyrimidine. This compound has unique chemical properties. The synthetic route is as follows. category: pyrimidines

Synthesis of methyl 1-methyl-4-(2-methylpyrimidin-4-yl)-1H-pyrazole-5-carboxylate Using 4-bromo-1-methyl-1H-pyrazole-5-carboxylic acid methyl ester (CAS No.: 514816-42-3, 2.0 g, 9.1 mmol) and 4-chloro-2-methylpyrimidine (0.94 g), methyl 1-methyl-4-(2-methylpyrimidin-4-yl)-1H-pyrazole-5-carboxylate (1.26 g) was obtained as a yellow oily substance using a method similar to that in in Working Example 3 or a method based on this method. (Physical property data) LC-MS: M=232, RT=0.75 (min), [M+H]+=233. 1H-NMR (300 MHz, CDCl3, delta ppm): 8.62 (1H, d, J=5 Hz), 7.85 (1H, s), 7.29 (1H, d, J=5 Hz), 4.15 (3H, s), 3.87 (3H, s), 2.74 (3H, s).

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, 4994-86-9, 4-Chloro-2-methylpyrimidine.

Reference:
Patent; MOCHIDA PHARMACEUTICAL CO., LTD.; SATOH, Tsutomu; KUDOH, Takashi; IWAMA, Tetsuo; (50 pag.)US2017/210740; (2017); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 4994-86-9, 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 4994-86-9 as follows.

General procedure: To a well stirred 8-aminoquinoline (1 mmol) indry DMF (5 mL), sodium hydride (1.2 mmol, 60% in mineral oil) was added at 0 C.After 10 min stirring, the corresponding heterocyclic chloro compound (1.2mmol) was added and stirred for 10 min at rt then heated at 60 C for 5-12 h.Upon completion, the reaction mixture was poured into crushed ice and theresulting solid was filtered, washed with water and dried under vacuum. Thesolid was triturated with methanol and dried under vacuum to afford targetcompound as a solid.

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:
Article; Kannan, Murugan; Raichurkar, Anandkumar V.; Khan, Fazlur Rahman Nawaz; Iyer, Pravin S.; Bioorganic and Medicinal Chemistry Letters; vol. 25; 5; (2015); p. 1100 – 1103;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia