4-Aminopyrimidine libraries from the Ugi-Smiles reaction of thiouracil

Madjid Ait Sidhoum (1) , Laurent El Kaim (2, 1) , Laurence Grimaud (3, 4)

1 DCSO - Laboratoire de synthèse organique
2 ENSTA Paris - École Nationale Supérieure de Techniques Avancées
3 PASTEUR - Processus d'Activation Sélective par Transfert d'Energie Uni-électronique ou Radiatif (UMR 8640)
4 LBM UMR 7203 - Laboratoire des biomolécules

The Ugi-Smiles reaction of S-benzyl thiouracil have been exploited in several three-step sequences for the preparation of aminopyrimidine libraries with high diversity. After the 4-component coupling, oxidation of the thioether to sulfone is followed by displacement of the latter by various carbon-centered nucleophiles (cyanide, malonate, boronic acids) or amines. The efficiency of the whole sequence was further demonstrated with one-pot procedures.

Keywords: Ugi-smiles; Pyrimidines; Sulfone; Suzuki reaction

Domains: Organic chemistry

Madjid Ait Sidhoum, Laurent El Kaim, Laurence Grimaud. 4-Aminopyrimidine libraries from the Ugi-Smiles reaction of thiouracil. Tetrahedron, 2018, 74 (38), pp.5222-5231. ⟨10.1016/j.tet.2018.04.058⟩. ⟨hal-02096394⟩