Regioselective synthesis of quinazoline containing novel monoaryl ethers at room temperature

We are herein reporting the regioselective synthesis of quinazoline containing novel monoaryl ethers (quinazoline-O-Ar) (3a-3j) at room temperature without any catalyst. From commercially available 2,4-dichloro-6,7-dimethoxyquinazoline (1), 4-chloro was selectively substituted with variety of electronically rich, electronically poor and electronically neutral phenols (2a-2j). Reaction was carried out in DMF and NaH for 4-6 hours at room temperature in fairly good yield. The products were purified (> 98% pure, hplc) by crystallization to avoid the use of column chromatography.