Synthesis of 6‐substituted pyrimidines by the wittig reaction. II . Via 2‐acetamido‐4‐hydroxy‐5‐phenylbutylpyrimidine‐6‐carboxaldehyde

Abstract

AbstractWittig condensations of both stabilized and unstabilized ylides were successfully achieved with 2‐acetamido‐4‐hydroxy‐5‐phenylbutylpyrimidine‐6‐carboxaldehyde (XI); functionalized Wittig reagents derived from dichloroacetone, ethyl 4‐iodobutyrate, 4‐bromobutyronitrile, phenylpropyl bromide, 3‐bromopropylphthalimide, p ‐ nitrobenzyl bromide, and p‐nitrocinnamyl bromide were used. The resultant 6‐substituted pyrimidines could be further transformed by reduction of the 6‐side‐chain double bond. Successful Wittig reactions were achieved with XI where the corresponding 2‐amino‐4‐hydroxy‐5‐phenylbutylpyrimidine‐6‐carboxaldehyde (X) with its less electrophilic aldehyde group failed to give isolable yields of condensation products.