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16.12.4.1.4.8.5 Exchange of Hydroxy for Amino

DOI: 10.1055/sos-SD-116-00063

von Angerer, S.Science of Synthesis Knowledge Updates, (20111427.

Exchange of hydroxy groups for tertiary amino groups on aromatic and heteroaromatic rings can be achieved by the Ugi–Smiles coupling reaction. This reaction comprises four components: a phenol, an alkyl isocyanide, a primary amine, and an aldehyde, which are added to the solvent together at the same time. A number of substituted pyrimidin-4(3H)-ones 697 as the phenol component react with cyclohexyl isocyanide, benzyl- or allylamines, and aromatic or aliphatic aldehydes to give N,N-disubstituted pyrimidin-4-amines 698 in good to moderate yields (Scheme 391). This method is superior to any sequential reaction leading to the desired products.[‌1131‌,‌1132‌] 4-Methylpyrimidin-2(1H)-one, however, gives the corresponding amino-substituted pyrimidine only in low yield.

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M8 M8 Meeee (%) Mee
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