Category: 51957-32-5

Synthetic Route of 51957-32-5, 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. 51957-32-5, name is 4-Chloro-5-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.

[0485] Procedure: To a stirred solution of compound (2-(piperidin-4-yl)ethyl)sulfamide hydrochloride (0.1 g, 0.41 mmol) in DMF (4 mL) was added 4-chloro-5-methylpyrimidine (0.058 g, 0.45 mmol) and aqueous solution of potassium carbonate (0.113 g, 0.82 mmol) and the resulting mixture was stirred at 90 C for 12 h. The progress of the reaction was monitored by TLC. Then the reaction was quenched with water (20 mL) and extracted with ethyl acetate (2 × 30 mL). The combined organic layers were washed with brine (30 mL), dried over sodium sulphate, filtered and evaporated under reduced pressure. The crude obtained was purified by combiflash purifier using ethyl acetate in n-hexane to afford N-(2-(1-(5-methylpyrimidin-4-yl)piperidin-4-yl)ethyl)sulfamide (0.012 g , 9.83 %).1HNMR (400 MHz, DMSO-d6): delta 8.44 (s, 1H), 8.09 (s, 1H), 6.42 (s, 2H), 6.39 (t, J = 6 Hz, 1 H), 3.93 (d, J = 13.2 Hz, 1H), 2.90 (q, J = 7.2 Hz, 2H), 2.80 (t, J = 12.4 Hz, 2H), 2.15 (s, 3H), 1.70 (d, J = 12.8 Hz, 2H), 1.58-1.63 (m, 1H), 1.41(q, J = 6.8 Hz, 2H), 1.11-1.21-(m, 2H). LC-MS (ES) m/z = 300.1 [M+H]+.

According to the analysis of related databases, 51957-32-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MAVUPHARMA, INC.; GALLATIN, William Michael; ODINGO, Joshua; DIETSCH, Gregory N.; FLORIO, Vincent; VENKATESHAPPA, Chandregowda; DURAISWAMY, Athisayamani Jeyaraj; (273 pag.)WO2019/46778; (2019); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

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. 51957-32-5, name is 4-Chloro-5-methylpyrimidine, the common compound, a new synthetic route is introduced below. Computed Properties of C5H5ClN2

A 2 M aqueous Na2CO3 solution (1 .51 ml_) is added to a mixture of 4-chloro-5- methyl-pyrimidine (186 mg) and 4-boronobenzoic acid (200 mg) in N,N- dimethylformamide (5 ml_). The mixture is sparged with argon for 3 min and [1 ,1 ‘- bis(diphenylphosphino)-ferrocene]dichloropalladium dichloromethane complex (100mg) is added. The resulting mixture is stirred at 80C overnight. After cooling to room temperature, water is added and the mixture is treated with charcoal. The solids are filtered off and rinsed with water. The filtrate is extracted with ethyl acetate. The aqueous phase is acidified with 4 M hydrochloric acid and extracted with ethyl acetate. The combined extracts are dried over MgSO4 and concentrated in vacuo. The residue is triturated with diisopropyl ether and the precipitate is filtered off and dried to give the title compound. LC (method 4): tR = 0.77 min; Mass spectrum (EST): m/z = 215 [M+H]+.

The synthetic route of 51957-32-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; NEUROCRINE BIOSCIENCES, INC.; NOSSE, Bernd; BLUM, Andreas; HECKEL, Armin; HIMMELSBACH, Frank; ASHWEEK, Neil J.; HARRIOTT, Nicole; WO2014/37327; (2014); A1;,
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. 51957-32-5, name is 4-Chloro-5-methylpyrimidine. This compound has unique chemical properties. The synthetic route is as follows. Computed Properties of C5H5ClN2

General procedure: EtOH (1.9 mL) was added into a mixture of Intermediate 1J (100 mg, 0.24 mmol), B2(OH)4 (64 mg, 0.71 mmol), XPhos-Pd-G2 (19 mg, 0.024 mmol), XPhos (23 mg, 0.048 mmol), and KOAc (70 mg, 0.71 mmol). The reaction was degassed with N2 and stirred at 80C for approximately 55 minutes. After cooling to room temperature, methyl 4- chloronicotinate hydrochloride (64 mg, 0.31 mmol) and K2C03 (1.8 M, 400 mu, 0.71 mmol) were added respectively. The reaction was degassed with N2 again, stirred at 85C for approximately 3 hours, and cooled to room temperature. The reaction was filtered through celite and washed with EtOAc (3X). The combined organic layers were washed with brine (IX), dried over sodium sulfate, filtered, and concentrated in vacuo. The residue was purified by silica gel chromatography (0 – 100% EtOAc/Hexanes) to afford the title compound (70 mg, 61%). LCMS (method A): m/z 479.5 (M+H)+. 1H NMR (CDCI3) delta 9.00 (s, IH), 8.72 (d, IH), 7.82 (d, IH), 7.77 (d, IH), 7.55 (t, IH), 7.47 (t, IH), 7.29 (m, 2H), 7.21-7.14 (m, 3H), 5.18 (s, IH), 3.77 (s, 3H), 1.68 (s, 6H).

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, 51957-32-5, 4-Chloro-5-methylpyrimidine.

Reference:
Patent; VENENUM BIODESIGN LLC; HUANG, Chia-Yu; SHI, Dongchuan; KULTGEN, Steven G.; MCGUINNESS, Brian F; LETOURNEAU, Jeffrey J.; COLE, Andrew G.; BEASLEY, James R.; (358 pag.)WO2018/5801; (2018); A2;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia