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Synthesis of 6‐substituted pyrimidines by the wittig reaction. I . Via 2‐amino‐4‐hydroxy‐5‐phenylbutylpyrimidine‐6‐carboxaldehyde
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.5570030315
Subject(s) - phosphorane , wittig reaction , chemistry , isopropyl , reagent , yield (engineering) , hydrolysis , organic chemistry , condensation , carbodiimide , stereochemistry , medicinal chemistry , materials science , physics , metallurgy , thermodynamics
Condensation of isopropyl 6‐phenylhexanoate with ethyl diethoxyacetate followed by guanidine afforded 2 ‐ amino‐6‐diethoxymethyl‐5‐phenylbutyl‐4‐pyrimidinol (VII). Acid hydrolysis of VII gave an excellent yield of 2‐amino‐4‐hydroxy‐5‐phenylbutylpyrimidine‐6‐carboxaldehyde (IV); the latter could be condensed with stabilized Wittig reagents such as carbethoxymethylene triphenyl phosphorane and cinnamylidene triphenyl phosphorane, but not unstabilized Wittig reagents such as carbethoxypropylene or cyano‐propylene triphenyl phosphorane. Reduction of the Wittig products afforded pyrimidines with functionalized side‐chains in the 6‐position such as the 6‐phenylbutyl (XVIII) and 6‐carboxyethyl (XV) derivatives of 2‐amino‐5‐phenylbutyl‐4‐pyrimidinol.