Traceless solid-phase synthesis of 2,4-diaminoquinazolines.
[reaction: see text] The solid-phase synthesis of 2,4-diaminoquinazolines is presented. The chemistry involves the sequential condensation of 2-aminobenzonitriles and amines starting from an acyl isothiocyanate resin via a traceless cleavage and cyclization. The alpha-1 antagonist prazosin was synthesized, as well as several other examples, in good yields and purity.
Wilson
L J
LJ
Procter & Gamble Pharmaceuticals, Healthcare Research Center, Mason, Ohio 45040, USA. lwilson3@prius.jnj.com
D000317:Adrenergic alpha-Antagonists / Q000138:chemical synthesis* / Q000737:chemistry; D000588:Amines / Q000737:chemistry; D003500:Cyclization; D017879:Isothiocyanates / Q000737:chemistry; D009570:Nitriles / Q000737:chemistry; D011224:Prazosin / Q000138:chemical synthesis* / Q000737:chemistry; D011799:Quinazolines / Q000138:chemical synthesis* / Q000737:chemistry; D012116:Resins, Plant / Q000737:chemistry
D000317:Adrenergic alpha-Antagonists; D000588:Amines; D017879:Isothiocyanates; D009570:Nitriles; D011799:Quinazolines; D012116:Resins, Plant; C013474:2,4-diaminoquinazoline; C037152:isothiocyanic acid; D011224:Prazosin