Journal of Heterocyclic Chemistry p. 183 - 185 (2000)
Update date:2022-08-04
Topics:
Samano, Vicente
Styles, Virgil L.
Chan, Joseph H.
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.
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