Chemical and Pharmaceutical Bulletin p. 683 - 685 (1995)
Update date:2022-08-16
Topics:
Sano
Ishihara
Yoshihara
Sumino
Nawa
A facile and practical synthesis of 9-methyl-3-(1H-tetrazol-5-yl)-4H-pyrido[1,2-a]pyrimidin-4-one (4), the potassium salt of which is used clinically as an anti-asthma agent, is described. Treatment of a key intermediate (6b), prepared from 2-amino-3-methylpyridine (1) and 2-ethoxymethylene-1,3-propanedinitrile, with sodium azide in N,N-dimethylformamide gave predominantly the cyanotetrazole (7a), while in acetic acid it gave exclusively the iminotetrazole (7b), which was easily converted into 4 by acid hydrolysis. A one-pot process starting from 6b to give 4, avoiding the use of explosive aluminum azide, was established.
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