Tetrahedron Letters (2019)
Update date:2022-08-04
Topics:
Tian, Xinrong
Suarez, Dominic P.
Li, William Hoi Hong
McSherry, Allison K.
Sanchez, Robert M.
Moore, Michael L.
Axten, Jeffrey M.
We describe an efficient synthesis of 2,4-substituted pyrido[4,3-d]pyrimidin-5(6H)-ones, which involves the acid-promoted cyclization of cyano enamine 15 to afford 2,4-bis(methylthio)pyrido[4,3-d]pyrimidin-5(6H)-one 17 as a key intermediate. Selective displacement of the 4-methylthio group by a wide range of anilines followed by oxidation of the 2-methylthio group and subsequent substitution by amines enabled the synthesis of a variety of 2,4-disubstituted pyrido[4,3-d]pyrimidin-5(6H)-ones.
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