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

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.