Article ID | Journal | Published Year | Pages | File Type |
---|---|---|---|---|
5267413 | Tetrahedron Letters | 2012 | 5 Pages |
Abstract
2,4-Disubstituted-5-fluoropyrimidine is a biologically active molecular core seen in various anticancer agents such as 5-fluorouracil (5-FU). As part of a programme aimed at discovering kinase inhibitors, routes to two series of novel compounds (5-fluoropyrimidine-2-carboxamides and 5-fluoropyrimidine-4-carboxamides) were successfully executed. For the first series, regioselective substitution at the 4-position of the pyrimidine with an amine (HNR1R2) was achieved, followed by preparation of the amide at the 2-position. The route to the second series involved introduction of the methoxy protecting group at the 4-position, which allowed subsequent amine substitution to occur at the 2-position. The 4-amide substituent was finally introduced by direct conversion of the 4-methoxy into a 4-chloro group followed by transformation into an amide by palladium catalysis.
Related Topics
Physical Sciences and Engineering
Chemistry
Organic Chemistry
Authors
Hiroki Wada, Lili Cheng, Ji Jiang, Zhigan Jiang, Jun Xie, Tao Hu, Hitesh Sanganee, Tim Luker,