Utility of [4‐(3‐methoxyphenyl)pyrimidin‐2‐yl]cyanamide in synthesis of some heterocyclic compounds

Abstract

AbstractN‐[4‐(3‐Methoxyphenyl)pyrimidin‐2‐yl]cyanamide (1) was reacted with morpholine and respective binuclephilic reagents namely: ethylenediamine, o‐phenylenediamine, o‐aminothiophenol, or o‐aminophenol to give the corresponding carboximidamide 2, imidazolidine 3, and benzazoles 4–6. While its reaction with hydrazides in DMF at 90°C, gave the corresponding 1,2,4‐triazols 7–11. Also, treatment of cyanamide 1 with heterocycles having both nucleophilic and electrophilic groups (─NH2/─COOEt) in iso‐propanol in presence of catalytic amount of Conc. HCl, gave the corresponding thieno[2,3‐d]pyrimidinone 12 and unexpected thieno[3,2‐d]pyrimidine 13 instead of bis‐thieno[3,2‐d]pyrimidine 14, respectively. While, its reaction with ethyl 5‐amino‐1,3‐thiazole‐4‐carboxylate yielded the unexpected N‐(pyrimidin‐2‐yl)urea 15 rather than the corresponding thiazolo[5,4‐d]pyrimidine 16. Unexpected N‐(pyrimidin‐2‐yl)thiourea 17 was obtained, when cyanamide 1 reacted with potassium thiolates in iso‐propanol with catalytic amount of Conc. HCl.