Synthesis of pyrrolo[2,3-d]pyrimidines with 3-amino-2-hydroxypropyl substituents

Synthesis, QSAR modeling, and molecular docking of novel fused 7‐deazaxanthine derivatives as adenosine A2A receptor antagonists

“…A variety of the alkyl residues was introduced in the last step of the synthetic route – the diazepine ring closure with various primary aliphatic amines. First, methyl 1,3‐dimethyl‐2,4‐dioxo‐2,3,4,7‐tetrahydro‐1 H ‐pyrrolo[2,3‐ d ]pyrimidine‐6‐carboxylate 1 was converted into 8‐(bromomethyl)‐2 H ‐pyrimido[5′,4′:4,5]pyrrolo[2,1‐ c ][1,4]oxazine 3 according to the previously described methods (Muzychka et al, 2012; Yaremchuk et al, 2018). Upon a brief heating of compound 3 with sodium methoxide in methanol, it was transformed into methyl 1,3‐dimethyl‐7‐(oxiran‐2‐ylmethyl)‐2,4‐dioxo‐2,3,4,7‐tetrahydro‐1 H ‐pyrrolo[2,3‐ d ]pyrimidine‐6‐carboxylate 4 .…”