Category: 209959-33-1

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 209959-33-1, name is 2-[Bis(tert-Butoxycarbonyl)amino]-5-bromopyrimidine. This compound has unique chemical properties. The synthetic route is as follows. Application In Synthesis of 2-[Bis(tert-Butoxycarbonyl)amino]-5-bromopyrimidine

Step B: A mixture of 2-[bis(tert-butoxycarbonyl)amino]-5-bromopyrimidine (3.0 g, 8.0 mmol), dimethylzinc (1.2 M×8.0 mL, 9.6 mmol) and [1,1?-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (130 mg, 0.16 mmol) in 1,4-dioxane (30 mL) was stirred at 110 C. for 16 h under Argon. The mixture was cooled to room temperature, diluted with ethyl acetate and washed with saturated NH4Cl, water and brine. The organic layer was dried over NaSO4, concentrated and purified by silica gel column chromatography (0-35% EtOAc in hexanes) to give a white solid, which was dissolved in trifluoroacetic acid (5.0 mL). After 5 min, the solvent was removed and the residue was partitioned between ethyl acetate and an aqueous saturated NaHCO3 solution. The organic layer was dried over NaSO4, filtered and concentrated to give the title compound (0.7 g, 80%) as a white solid. MS m/z 110.1 [M+H]+.

With the rapid development of chemical substances, we look forward to future research findings about 209959-33-1.

Reference:
Patent; PTC Therapeutics, Inc.; F. Hoffmann-La Roche AG; Woll, Matthew G.; Chen, Guangming; Choi, Soongyu; Dakka, Amal; Huang, Song; Karp, Gary Mitchell; Lee, Chang-Sun; Li, Chunshi; Narasimhan, Jana; Naryshkin, Nikolai; Paushkin, Sergey; Qi, Hongyan; Turpoff, Anthony A.; Weetall, Marla L.; Welch, Ellen; Yang, Tianle; Zhang, Nanjing; Zhang, Xiaoyan; Zhao, Xin; Pinard, Emmanuel; Ratni, Hasane; (317 pag.)US9617268; (2017); B2;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 209959-33-1, 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. 209959-33-1, name is 2-[Bis(tert-Butoxycarbonyl)amino]-5-bromopyrimidine. A new synthetic method of this compound is introduced below.

3- (2-bis-tert-Butoxycarbonylamino-pyrimidin-5-yl)-acrylic acid tert-butyl ester:; A mixture of (5-bromo-pyrimidin-2-yl) -bis-carbamic acid tert-butyl ester (5.0 g, 13.4 mmol), tert- butylacrylate (3.9 mL, 26.7 mmol), potassium acetate (3.9 g, 40.2 mmol), tetrabutylammonium bromide (4.3g, 13.4 mmol), palladium acetate (150 mg, 0.7 mmol), and N-N’-dimethylformamide (50 mL) was stirred at 70 C for 1 h. Solvent removed under vacuum, and residue partitioned between ether (200 mL) and water. Organic washed further with water and saturated ammonium chloride then dried over magnesium sulfate. Product isolated as a yellow solid after purification on silica. M+1=422.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,209959-33-1, 2-[Bis(tert-Butoxycarbonyl)amino]-5-bromopyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; AMGEN INC.; WO2005/70932; (2005); 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. 209959-33-1, name is 2-[Bis(tert-Butoxycarbonyl)amino]-5-bromopyrimidine. This compound has unique chemical properties. The synthetic route is as follows. Product Details of 209959-33-1

(5) To a suspension of the compound (610 mg) obtained in (4) above in methanol (12 ml) is added sodium hydride (60%, 130 mg), and the mixture is refluxed for 1 hour. The reaction solution is neutralized with aqueous 2N hydrochloride solution. The mixture is diluted with water, and precipitated solids are collected, washed with water, ether, and hexane to give 2-methylthio-7,8-dihydro-7-oxo-pyrido[2,3-d]pyrimidine (481 mg) as powder. M.p. 270-271 C, MS (m/z) : 194 (MH+). IR(nujol):1672, 1608, 1597, 1525, 1460, 1383, 1167 cm-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, 209959-33-1, 2-[Bis(tert-Butoxycarbonyl)amino]-5-bromopyrimidine.

Reference:
Patent; TANABE SEIYAKU CO., LTD.; EP1364950; (2003); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 209959-33-1, 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. 209959-33-1, name is 2-[Bis(tert-Butoxycarbonyl)amino]-5-bromopyrimidine, molecular formula is C14H20BrN3O4, 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.

Example 15 tert-Butyl 5-bromopyrimidin-2-ylcarbamate 11 To a solution of 2-[bis(tert-butoxycarbonyl)amino]-5-bromopyrimidine 10 (216 kg crude, 460 mol, assuming quantitative yield in previous step) in anhydrous ethanol (1692 L) was slowly added a solution of sodium hydroxide (55.2 kg, 1380 mol) in water (344 L) while maintaining the temperature at 0-20 C. The mixture was stirred at that temperature until the content of 2-[bis(tert-butoxycarbonyl)-amino]-5-bromopyrimidine (10) was ?0.5% by HPLC. The reaction mixture was cooled to 0-5 C. and the pH was adjusted to 7 by addition of oxalic acid (86.0 kg, 955 mol) while maintaining the temperature below 5 C. The mixture was then distilled under vacuum to a volume of 500-600 L while controlling the temperature below 50 C. Water (800 kg) was added and the mixture was stirred for 1 h. The solid was collected by filtration and stirred with water (2*500 L). The resulting solid was collected by filtration and dried under reduced pressure at 50 C. to afford tert-butyl 5-bromopyrimidin-2-ylcarbamate 11 (107 kg, 85% yield over two steps). 1H NMR (500 MHz, CDCl3) delta 8.63 (s, 2H), 8.12 (s, 1H), 1.55 (s, 9H). LCMS (ESI) m/z [M+H-Boc] 176

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 209959-33-1, 2-[Bis(tert-Butoxycarbonyl)amino]-5-bromopyrimidine.

Reference:
Patent; Genentech, Inc.; Babu, Srinivasan; Cheng, Zhigang; Gosselin, Francis; Hidber, Pirmin; Hoffmann, Ursula; Humphries, Theresa; Reents, Reinhard; Tian, Qingping; Yajima, Herbert; US2014/100366; (2014); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia