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An improved synthesis of 2‐amino‐5‐[(4‐chlorophenyl)thio]‐4‐morpholinopyrimidine (BW 394U) — A potential antisenility agent
Author(s) -
Samano Vicente,
Styles Virgil L.,
Chan Joseph H.
Publication year - 2000
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.5570370131
Subject(s) - chemistry , morpholine , thio , yield (engineering) , reagent , stereochemistry , combinatorial chemistry , amino acid , medicinal chemistry , organic chemistry , biochemistry , materials science , metallurgy
This paper describes the synthesis of 2‐amino‐5‐[(4‐chlorophenyl)thio]‐4‐morpholinopyrimidine (BW 394U, compound 4 ), a potential antisenility agent. The key intermediates 3a/3b were obtained from an in situ ‐generated Vilsmeier‐Haack reagent that simultaneously protected the 2‐amino group prior to further manipulations. Displacement of the chloro group in 3a gave 4 in 40% yield and 4‐dimethylamino analogue 5. However, displacement of 3b with morpholine followed by treatment with aqueous base gave 4 in 74% yield.