Journal
MONATSHEFTE FUR CHEMIE
Volume 141, Issue 8, Pages 907-911Publisher
SPRINGER WIEN
DOI: 10.1007/s00706-010-0334-0
Keywords
Imatinib; 2-(Methylsulfonyl)pyrimidine derivatives; 4-(Chloromethyl)benzonitrile; Substitution
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Funding
- Shanghai Science and Technology Mission [10ZR1409600]
- Program for New Century Excellent Talents in University (NCET)
- Laboratory of Organic Functional Molecules, the Sino-French Institute of ECNU
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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 N2H4 center dot H2O/FeCl3 center dot 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.
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