2,6-Diaminopyridine → 2-Amino-5,7-dimethyl-1,8-naphthyridine

Participants

Reaction Steps

Preparation of the compounds having the formula: ##STR3## wherein R' is CH3, OH or CF3 is carried out by (a) condensing 2,6-diaminopyridine with 2,4-pentanedione to yield 7-amino-2,4-dimethyl-1,8-naphthyridine, (b) acetylating the naphthyridine to form the corresponding 7-acetamido naphthyridine, (c) methylating the 7-acetamido compound of step (b) to form a 1,2,4-trimethyl product, (d) hydrogenating the step (c) product to yield 7-acetamido-1,2,4-trimethyl-1,2,3,4-tetrahydro-1,8-naphthyridine, (e) hydrolyzing the product of step (d) under basic conditions and (f) condensing the product of step (e) with a β-diketone of the formula R'COCH2CO2H5 wherein R' is CH3, CH3 or OC2H5.

Provenance & Evidence