A relay Pd(0)/Brønsted base-catalyzed cascade reaction between N-trifluoroethyl isatin ketimines and propargylic carbonates is reported, proceeding through Pd(0)-catalyzed allenylation followed by Brønsted base-directed deprotonation, 5-endo-trig cyclization, ring expansion, and aromatization. A broad range of pyrrolopyrimidinone frameworks are furnished in high yields with good tolerance toward a variety of functional groups.