4-Aryl-Pyrimidin-2-Yl Tosylates as Efficient Reaction Partners: Application to the Synthesis of Pyrimidines Functionalised with Propargyloxy and 1,2,3-Triazolo Groups

Abstract

The 4-arylated pyrimidin-2-yl tosylate derivatives, easily prepared from cheap commercial materials, reacted efficiently with propargyl alcohol/NaOBu t to give the corresponding 4-arylated 2-propargyloxy-pyrimidine derivatives which, in a onepot reaction catalysed by CuSO 4 •5H 2 O/sodium ascorbate, reacted with NaN 3 and hexyl or benzyl bromide to give a series of 2-(1-hexyl-or 1-benzyl-1,2,3-triazol-4-yl)methoxy-pyrimidine derivatives in good yields.

N-Directed Pd-Catalyzed Photoredox-Mediated C–H Arylation for Accessing Phenyl-Extended Analogues of Biginelli/Suzuki-Derived Ethyl 4-Methyl-2,6-diphenylpyrimidine-5-carboxylates

“…Access to multi-substituted pyrimidines, by means of C2 modification of 3,4-DHPMs, to eventually form a C-heteroatom or C-C bond, requires prior aromatization of Biginelli products [10][11][12][13][14] and conversion of the resulting C2-OH to a good leaving group, such as halide or sulfonate (Scheme 1) [31][32][33]. This is eventually replaced by nucleophiles [34][35][36] or submitted to cross-coupling reactions [37][38][39][40].…”