Synthesis of 6‐substituted pyrimidines by the wittig reaction. III . Via 2‐amino‐4‐hydroxy‐5‐phenylbutyl‐6‐pyrimidylmethyl triphenyl phosphonium bromide

Abstract 2‐Amino‐6‐bromomethyl‐5‐phenylbutyl‐4‐pyrimidinol (IV) smoothly alkylated triphenyl phosphine, resulting in a 95% yield of the phosphonium salt (V). This Wittig reagent (V) readily condensed with p‐nitrobenzaldehyde, p‐nitrocinnamaldehyde, or cinnamalde‐hyde in N,N‐dimethylformamide to give the 6‐(p‐nitrostyryl) (X), 6‐(p‐nitrophenyl‐1,3‐butadien‐1‐yl) (VIH), and 6‐(phenyl‐1,3‐butadien‐1‐yl) (IX) pyrimidinols in 72, 67 and 44% yields, respectively. Catalytic reduction of VIII and IX afforded the corresponding 6‐(p‐aminophenylethyl) (XII) and 6‐(p‐aminophenylbutyl) (XI) 4‐pyrimidinols.