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2,4-disubstituted pyrimidines are important pharmacophore and synthetic motif, and have already embedded in the structures of several antihypertensives (doxazosin, prazosin, et al.) and tyrosine kinase inhibitors (imatinib, dasatinib, et al.).1 Among them, the 2,4-disubstituted pyrano[2,3-d]pyrimidines and furo[2,3-d]pyrimidines have shown their biological activities such as antimicrobial, antioxidant, and anticancer (Scheme 1).2 Despite the wide interest in these compounds, the synthetic methods remain limited. One of the most popular routes employs the nucleophilic attack from barbituric acid to 2-methylenemalononitriles or α-chloroketones (Scheme 1b, Route A),2b,2g,3 providing pyrimidiones for rapid reductive amination. Meanwhile, another prevailing route starts from the 2-amino-pyran(or furan)-3-carbonitriles affording 2,4-disubstituted products for biological assessment directly (Scheme 1b, Route B).2a,2j,4 Besides, Pd-catalyzed 5-endo-dig cyclization has also found their application in the synthesis of furo[2,3-d]pyrimidines.5 Abundant compounds have been synthesized using these strategies, however, the relative narrow structural diversity at 2,4-position constrained their further investigation. Although the synthetic friendly C-Cl bonds have been introduced, the harsh conditions are required for the transformation.6 Thus, it’s highly desired for a novel protocol providing pyrano[2,3-d]pyrimidines and furo[2,3-d]pyrimidines with 2,4-dichloro substituted, which may benefits the following functionalization.