Category: 14001-67-3

Synthetic Route of 14001-67-3, 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. 14001-67-3, name is 5-Bromo-2-methylthiopyrimidine. A new synthetic method of this compound is introduced below.

Step 1 After purged with nitrogen, mixture of 5-bromo-2-(methylthio)pyrimidine (1.0 g, 4.9 mmol), tris(dibenzylideneacetone)dipaliadium(0) (0.45 g, 0.49 mmol), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (0.56 mg, 0.98 mmol), cesium carbonate (2.38 g, 7.3 mmol) and dioxane (20 mL) was added to 4-(5-fluoro-2-pyridyloxy)aniline (1.0 g, 4.9 mmol), and stirred under heating at reflux for 24 hours. The reaction mixture was added to saturated chloride ammonium aqueous solution, and extracted with ethyl acetate. The organic phase was washed by saturated saline, dried over anhydrous sodium sulfate, and then concentrated in vacuo. The resulting residue was purified by silica-gel column chromatography (ethyl acetate/hexane). The resulting mixture was solidified by diisopropyl ether to give 5-[4-(5-fluoro-2-pyridyloxy)phenylamino]-2-(methylthio)pyrimidine (0.51 g, yield: 32%) as pale yellow solid. 1H-NMR (delta ppm TMS/CDCl3): 2.57 (3H, s), 5.48 (1H, s), 6.89-6.95 (1H, m), 7.03-7.11 (4H, m), 7.45 (1H, m), 8.02 (1H, s), 8.40 (2H, s).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,14001-67-3, its application will become more common.

Reference:
Patent; Shionogi & Co., Ltd.; KAI, Hiroyuki; TANAKA, Satoru; HIRAMATSU, Yoshiharu; NOZU, Azusa; NAKAMURA, Ken’ichioh; (260 pag.)US2016/24072; (2016); 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. 14001-67-3, name is 5-Bromo-2-methylthiopyrimidine, molecular formula is C5H5BrN2S, 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 5-Bromo-2-methylthiopyrimidine

Step 1: 2-Methylsulfanyl-5-phenylethynyl-pyrimidine Bis-(triphenylphosphine)-palladium(II)dichloride (120 mg, 0.16 mmol, 0.05 equiv.) were dissolved in 50 ml THF and 5-bromo-2-methylsulfanyl-pyrimidine (840 mg, 4.1 mmol) and phenylacetylene (410 mu, 4.1 mmol, 1 equiv.) were added at room temperature. Triethylamine (1.36 ml, 12.3 mmol, 3 equiv.), triphenylphosphine (28 mg, 0.12 mmol, 0.03 equiv.) and copper(I)iodide (19 mg, 0.08 mmol, 0.03 equiv.) were added and the mixture was stirred for 3 hours at 65C. The reaction mixture was cooled and extracted once with saturated NaHCC”3 solution and three times with ethyl acetate. The organic layers were combined, dried with sodium sulfate, filtered and evaporated to dryness. The crude product was purified by flash chromatography on silicagel (heptane: ethyl acetate 100:0 -> 50:50). The desired 2- Methylsulfanyl-5-phenylethynyl-pyrimidine was obtained as a light yellow solid (400 mg, 44%), MS: m/e = 227.3 (M+H+).

With the rapid development of chemical substances, we look forward to future research findings about 14001-67-3.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; JAESCHKE, Georg; LINDEMANN, Lothar; RICCI, Antonio; RUEHER, Daniel; STADLER, Heinz; VIEIRA, Eric; WO2013/50460; (2013); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 14001-67-3, 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 14001-67-3 as follows.

To a 100 mL one neck round bottom flask was charged with 2-methylthio-5- bromopyrimidine (1 g, 4.88 mmol) along with pinacoldiborane (1.362 g, 5.36 mmol), potassium acetate (0.957 g, 9.75 mmol), Pd(dppf)CH2C12 (0.178 g, 0.244 mmol) and DMSO (10 ml). The flask was sealed with septum and connected to manifold through a syringe needle. The system was vacuumed and refilled with nitrogen three times and the mixture wasthen stirred and heated in an oil bath of 100 OC for 6 hr. The reaction mixture was black. LCMS showed complete consumption of starting material. After cooled to room temperature, the residue was diluted with ethyl acetate (100 mL) and water (50 ml). The organic layer was separated and the aqueous layer was extracted with ethyl acetate (3x). The combined organic phases were washed with water, dried over Mg504, filtered and concentrated. The residue waspurified by MPLC (24 g silica gel, 10 to 60% ethyl acetate in hexanes) to afford ligh yellow solid product 2-(methylsulfanyl)-5 -(4,4,5,5 -tetramethyl- 1,3 ,2-dioxaborolan-2-yl)pyrimidine. LC-MS (ES, m/z): C11H17BN2025: 252; Found: 253 [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,14001-67-3, its application will become more common.

Reference:
Patent; MERCK SHARP & DOHME CORP.; DEVITA, Robert, J.; YU, Yang; LIU, Jian; HE, Shuwen; KRIKORIAN, Arto, D.; MILLER, Daniel, J.; WU, Zhicai; YANG, Ginger Xu-Qiang; HONG, Quingmei; LAI, Zhong; ZORN, Nicolas; TING, Pauline, C.; WO2013/130370; (2013); A2;,
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. 14001-67-3, name is 5-Bromo-2-methylthiopyrimidine. This compound has unique chemical properties. The synthetic route is as follows. Quality Control of 5-Bromo-2-methylthiopyrimidine

A mixture of azetidine (0.03 mL, 0.5 mmol), 5-bromo-2-(methylthio)pyrimidine (100 mg, 0.49 mmol),Xantphos (4,5-Bis(diphenylphosphino)-9,9-dimethylxanthene) (9.9 mg, 0.02 mmol), Pd(OAc)2 (2 mg, 0.01 mmol) and NaOt-Bu (140 mg, 1 .5 mmol) in toluene (1 .7 mL) was heated at 110C. After 3h, the reaction mixture was cooled to room temperature and concentrated under vacuum. Purification (FCC, 5i02, 0-99% EtOAc in hexanes) afforded the title compound (39 mg,44%). MS(ESl): mass calcd. forC8H11N3S, 181.1; m/zfound, 182.1 [M+H]. 1H NMR (400 MHz, DMSO-d5) O 7.96 (s, 2H), 3.87 (t, J = 7.3 Hz, 4H), 2.45 (s, 3H), 2.40 -2.32 (m, 2H).

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, 14001-67-3, 5-Bromo-2-methylthiopyrimidine.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; CHEN, Gang; CHROVIAN, Christa C.; COATE, Heather R.; DVORAK, Curt A.; GELIN, Christine F.; HISCOX, Afton; LETAVIC, Michael A.; RECH, Jason C.; SOYODE-JOHNSON, Akinola; STENNE, Brice; WALL, Jessica L.; ZHANG, Wei; (583 pag.)WO2017/139428; (2017); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia