A transition metal-free direct C–H silylation of pharmaceutically relevant pyrrolo[2,3-d]pyrimidine (7-DAPs) derivatives with hydrosilanes has been developed via a radical reaction. This protocol provides the divergent silylated 7-DAPs in moderate to good yields with good regioselectivity. The protocol features operational simplicity, broad substrate scope and the use of safe and readily available LPO (Lauroyl peroxide) as the radical initiators. Preliminary mechanistic studies suggest that the induced silyl radical is involved in this transformation.