A FACILE AND PRACTICAL SYNTHESIS OF 9-METHYL-3-(1H-TETRAZOL-5-YL)-4H-PYRIDO [1,2-A]PYRIMIDIN-4-ONE

A facile and practical synthesis of (1H-tetrazol-5-yl)-4H-pyrido[1,2-a ]pyrimidin-4-one (4), the potassium salt of which is used clinically a s 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 e xclusively the iminotetrazole (7b), which was easily converted into 4 by acid hydrolysis. A one-pot process starting from 6b to give 4, avoi ding the use of explosive aluminum azide, was established.