Category: 935534-47-7

Synthetic Route of 935534-47-7, 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. 935534-47-7, name is 5-Bromo-4-(trifluoromethyl)pyrimidin-2-amine. A new synthetic method of this compound is introduced below.

Synthesis of 5-(4,4,5,5-tetramethyl(l,3,2-dioxaborolan-2-yl))-4- (trifluoromethyl)pyrimidine-2-ylamine[0095] To a dry 500 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 (150 mL). Argon was bubbled through the solution for 15 minutes, at which time l,l’-bis(diphenylphosphino)ferrocene palladium (II) chloride (1.7 g, 2.1 mmol) was added. The reaction was refiuxed in a 115 C 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 Si02 chromatography (30-40% EtOAc/hexanes) yielding 4.40 g of an off white solid. By ? 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). l NMR (CDC13): delta 8.72 (s, 1H), 5.50 (bs, 2H), 1.34 (s, 12H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,935534-47-7, its application will become more common.

Reference:
Patent; DANA-FARBER CANCER INSTITUTE, INC.; ZHAO, Jean J.; WANG, Qi; WO2012/109423; (2012); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

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