Studies on Pyrimidine Derivatives. XXXVIII. Cross-Coupling Reaction of N-Heteroaryl Iodides with Ethoxycarbonylmethylzinc Bromide in the Presence of Palladium Catalyst

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In the presence of tetrakis (triphenylphosphine) palladium, 2-iodo-4, 6-dimethylpyrimidine and 4-iodo-2, 6-dimethylpyrimidine reacted with ethoxycarbonylmethylzinc bromide (Reformatsky reagent) to give ethyl 4, 6-dimethyl-2-pyrimidineacetate and ethyl 2, 6-dimethyl-4-pyrimidineacetate, respectively. In contrast, the reaction of 5-iodo-2, 4-dimethylpyrimidine with the same reagent resulted in recovery of the starting iodide. Similar results were observed in the reactions of various N-heteroaryl iodides.