935534-47-7 , The common heterocyclic compound, 935534-47-7, name is 5-Bromo-4-(trifluoromethyl)pyrimidin-2-amine, molecular formula is C5H3BrF3N3, its 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.
[0252] To a dry 50O mL flask was added 5-bromo-4-(trifluoromethyl)-2- pyrimidylamine (10.1 g, 41.7 mmol), potassium acetate (12.3 g, 125.2 mmol), 4,4,5,5- tetramethyl-2-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)-l,3,2-dioxaborolane (11.6 g, 45.9 mmol) and dioxane (15O mL). Argon was bubbled through the solution for 15 minutes, at which time l,l’-bis(diphenylphosphino)ferrocene palladium (H) chloride (1.7 g, 2.1 mmol) was added. The reaction was refluxed in a 115 0C oil bath for 6 hours under argon. After cooling to room temperature, the dioxane was removed in vacuo. EtOAc (500 mL) was added and the resulting slurry was sonicated and filtered. Additional EtOAc (500 mL) was used to wash the solid. The combined organic extracts were concentrated and the crude material was purified by SiO2 chromatography (30-40% EtOAc/hexanes) yielding 4.40 g of an off white solid. By 1H NMR the material was a 1:1 mixture of boronate ester and 2-amino-4-trifluoromethylpyrimidine byproduct. The material was used as is in subsequent Suzuki reactions. LCMS (m/z): 208 (MH+ of boronic acid, deriving from in situ product hydrolysis on LC). 1H NMR (CDCI3): delta 8.72 (s, IH), 5.50 (bs, 2H), 1.34 (s, 12H).
The synthetic route of 935534-47-7 has been constantly updated, and we look forward to future research findings.
Reference:
Patent; NOVARTIS AG; WO2007/84786; (2007); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia