Analyzing the synthesis route of 209959-33-1

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.

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