A novel synthesis of imatinib and its intermediates

A convenient method has been developed for the synthesis of imatinib and two of its intermediates. N -(2-Methyl-5-nitrophenyl)-4-(3-pyridyl)-2-pyrimidinamine, obtained from 2-(methylsulfonyl)-4-(3-pyridyl)pyrimidine via nucleophilic substitution, was reduced by N 2 H 4 ·H 2 O/FeCl 3 ·6H 2 O/C in 92%...

Full description

Saved in:
Bibliographic Details
Published in:Monatshefte für Chemie 2010-08, Vol.141 (8), p.907-911
Main Authors: Liu, Haiyan, Xia, Wenpin, Luo, Yu, Lu, Wei
Format: Article
Language:English
Subjects:
Analytical Chemistry
Chemistry
Chemistry and Materials Science
Chemistry/Food Science
Inorganic Chemistry
Organic Chemistry
Original Paper
Physical Chemistry
Theoretical and Computational Chemistry
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:A convenient method has been developed for the synthesis of imatinib and two of its intermediates. N -(2-Methyl-5-nitrophenyl)-4-(3-pyridyl)-2-pyrimidinamine, obtained from 2-(methylsulfonyl)-4-(3-pyridyl)pyrimidine via nucleophilic substitution, was reduced by N 2 H 4 ·H 2 O/FeCl 3 ·6H 2 O/C in 92% yield. The resulting amine was condensed with 4-[(4-methylpiperazin-1-yl)methyl]benzoic acid dihydrochloride, which was prepared from 4-(chloromethyl)benzonitrile via substitution and hydrolysis reactions, to provide the final product imatinib in good yield and high purity. Graphical abstract
ISSN:0026-9247
1434-4475
DOI:10.1007/s00706-010-0334-0