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

Baker B. R. | Zendy; Jordaan Johannes H. | Zendy

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

Author(s) -

Baker B. R.,

Jordaan Johannes H.

Publication year - 1966

Publication title -

journal of heterocyclic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.321

H-Index - 59

eISSN - 1943-5193

pISSN - 0022-152X

DOI - 10.1002/jhet.5570030317

Subject(s) - chemistry , wittig reaction , phosphonium , reagent , bromide , phosphine , yield (engineering) , medicinal chemistry , alkylation , dimethylformamide , phosphonium salt , phosphonate , phosphorane , catalysis , organic chemistry , materials science , solvent , metallurgy

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.

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