A short and unequivocal synthesis of 5-aminotetrazolo[1,5-a]-quinazoline as a tricyclic analogue of 4-(3-bromoanilino)-6,7-dimethoxyquinazoline (PD 153035)

The discovery of 4-(3-bromoanilino)-6,7-dimethoxyquinazoline (PD 153035) as an extremely potent inhibitor of the tyrosine kinase activity of the epidermal growth factor receptor led to the preparation of several fused tricyclic quinazoline analogues. The present paper reports a new tricyclic derivative: 5-(3-bromoanilino)-7,8-dimethoxytetrazolo1,5-a]quinazoline. This compound was synthesized by two different pathways viaa 1,3-dipolar cycloaddition of an azide at carbon 2 of the quinazoline ring.