Imatinib synthesis

7synthesis methods

Product Name:Imatinib
CAS Number:152459-95-5
Molecular formula:C29H31N7O
Molecular Weight:493.6

Cuiling Wang and colleagues reported a method for imatinib synthesis[1]. It is described by using the C–N coupling reaction of 4-(4-methylpiperazine-1-methyl)benzamide with N-(5-bromo-2-tolyl)-4-(3-pyridyl)pyrimidin-2-amine to form imatinib. In this synthetic route, the high efficiency and high selectivity of nano-ZnO as a catalyst is key to the mild hydrolysis of 4-(4-methylpiperazine-1-methyl)benzonitrile into the corresponding amide. The total imatinib yield was 51.3%, and the purity was 99.9%.
Imatinib synthesis

368879-17-8
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201230-82-2 Synthesis

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152460-10-1 Synthesis

N-(5-Amino-2-methylphenyl)-4-(3-pyridyl)-2-pyrimidineamine

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152459-95-5
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Yield:152459-95-5 95.8%

Reaction Conditions:

with palladium diacetate;triethylamine;4,5-bis(diphenylphosphino)-9,9-dimethylxanthene in 1,4-dioxane at 50; under 760.051 Torr; for 36 h;Inert atmosphere;Reagent/catalyst;Solvent;Temperature;

Steps:

1-4 Example 3

N-(5-amino-2-methylphenyl)-4-(pyridin-3-yl)pyrimidin-2-amine 0.1mol, 1-[(4-bromophenyl)methyl]-4-methyl 0.1mol of piperazine, 5mmol of palladium acetate, 5mmol of 4,5-bisdiphenylphosphine-9,9-dimethylxanthene and 0.18mol of triethylamine were added to 200mL of dioxane and replaced with nitrogen twice, Replace it with carbon monoxide twice, and heat to 50° C. under a carbon monoxide atmosphere (1 atm) with stirring for 36 hours. After the reaction is completed, the temperature is cooled down and replaced with nitrogen. The reaction solution is poured into 1L of water and filtered with suction. The obtained solid is recrystallized with methanol/dichloromethane (1/3, V/V). An off-white solid was obtained with a yield of 95.8%

References:

CN112125882,2020,A Location in patent:Paragraph 0033; 0041-0048