Synthetic Route of 5900-13-0,Some common heterocyclic compound, 5900-13-0, name is 5-Bromo-3-methoxypyrazin-2-amine, molecular formula is C5H6BrN3O, 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 B-79: Preparation of 3-{4-[3-(5-Amino-6-methoxy-pyrazin-2-yl)-1-(2,2-difluoro-ethyl)-1H- pyrazol-4-yl]-pyrimidin-2-ylamino}-propionitrilePreparation of B-79-2:To a solution of 5-bromo-3-methoxypyrazin-2-amine (4.50 g, 19.8 mmol) and 4-(dimethylamino)pyridine (1.24g, 10.1 mmol) in 70ml THF was added di-terf-butyldicarbonate (10.4 g, 47.6 mmol) and the reaction mixture was stirred at room temperature for 5.5 hour. The solvents were removed under reduced pressure and the residue was flash chromed on silica gel eluting 3:1 Hexanes/EtOAc to give B-79-2 as a white solid (5.403g, 67%). Example 1-1 : Preparation of (2S)-1-({4-[3-(5-amino-6-methoxypyrazin-2-yl)-1-(2,2-difluoroethyl)-1H- pyrazol-4-yl]pyrimidin-2-yl}amino)propan-2-olPreparation of 1-1-11-1-1 To a solution of 5-bromo-3-methoxypyrazin-2-amine (4.05g, 19.8mmol) in 70 mL dry THF was added DMAP (1.24g, 10,1 mmol) followed by boc anhydride (10.4g, 47.6mmol) in one portion at room temperature. The resulting mixture was allowed to stir at room temperature. When the starting material was gone by TLC, the reaction mixture was concentrated under reduced pressure to an amber oil. A precipitate developed when the oil residue was slurried in 3:1 Hexanes/EtOAc which was collected. The precipitate was dissolved in EtOAc and washed with saturated aqueous NaCI with some 0.5N HCI so pH was -5. The organic layer was dried over MgSO4 and cone. The crude product was purified by silica gel chromatography (eluting 3:1 Hexanes/EtOAc) to give 5.4Og of compound 1-1-1 as a white solid. 1 H NMR (400 MHz, DMSO-d6) delta ppm 1.36 (s, 18 H) 3.99 (s, 3 H) 8.37 (s, 1 H).
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Bromo-3-methoxypyrazin-2-amine, its application will become more common.