1206604-20-7

Basic information

• Product Name: N-5-bromo-2-methylphenyl(4-pyridine-3-yl)pyrimidine-2-amine
• Synonyms: N-5-bromo-2-methylphenyl(4-pyridine-3-yl)pyrimidine-2-amine
• CAS NO: 1206604-20-7
• Molecular Weight: 341.21
• Mol File: 1206604-20-7.mol

Chemical Properties

• CAS DataBase Reference: N-5-bromo-2-methylphenyl(4-pyridine-3-yl)pyrimidine-2-amine(CAS DataBase Reference)
• NIST Chemistry Reference: N-5-bromo-2-methylphenyl(4-pyridine-3-yl)pyrimidine-2-amine(1206604-20-7)
• EPA Substance Registry System: N-5-bromo-2-methylphenyl(4-pyridine-3-yl)pyrimidine-2-amine(1206604-20-7)

Safety Data

• Hazardous Substances Data: 1206604-20-7(Hazardous Substances Data)

Upstream product

• 55314-16-4 3-(N,N-dimethylamino)-1-(pyridin-3-yl)prop-2-en-1-one 
• 1206604-19-4 5-bromo-2-methylphenylguanidine nitrate 

Downstream Products

• 152459-95-5 imatinib 
• 641571-10-0 nilotinib 

Relevant articles and documents

Synthesis of Imatinib by C-N Coupling Reaction of Primary Amide and Bromo-Substituted Pyrimidine Amine

A new method for imatinib synthesis 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%. This simple and effective synthetic pathway avoids gene-impurity production (as classified by the FDA Center for Drug Evaluation and Research), and the synthesis is environmentally friendly with a short reaction time.

A PROCESS FOR THE PREPARATION OF IMATINIB

A process for the preparation of Imatinib according to the invention consists in converting the 2-methyl-5-halogenoaniline of the Formula 2 into the salt of the 2-methyl-5- halogenophenylguanidine of the Formula 3, which is then condensed with the 3-diaIkylamino- ]-(pyridin-3-yI)prop-2-en-l-one of the Formula 4 to yield the N-(2-methyl-5- halogenophenyl)-4-(pyridin-3-yl)-pyrimidin-2-ylamine of the Formula 5, which is then reacted with 4-(4-methylpiperazin-l-ylmethyl)benzamide of the Formula 6, and the obtained Imatinib is optionally converted into its addition salt.