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Synthesis of pyrimidinyl arylglycines through subsequent Mitsunobu and Petasis reactions |
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| Authors: | David Font José M Villalgordo |
| Institution: | a Department of Chemistry, Faculty of Sciences, University of Girona, Campus de Montilivi, E-17071 Girona, Spain b Villapharma Research, Polígono Industrial Oeste, c/Paraguay, Parcela 7/5-A, Módulo A, E-30169 Murcia, Spain |
| Abstract: | The synthesis of highly functionalized pyrimidinyl arylglycines is presented. The highlight in our synthetic sequence includes selective O-alkylation of 2-(benzylsulfanyl)-4(3H)-pyrimidinones with N-Boc β-aminoalcohols under Mitsunobu conditions, Petasis reaction with glyoxylic acid and phenylboronic acid and nucleophilic ipso-substitution of the activated sulfur with morpholine. The unexpected spontaneous Smiles rearrangement of several pyrimidinyl amines is also discussed. |
| Keywords: | Arylglycines Pyrimidines Mitsunobu reaction Petasis reaction Smiles rearrangement Nucleophilic ipso-substitution |
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