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I've seen many papers (see e.g. Synthesis 2010, 16, 2721–2724) in which the 4-chloro group of 2,4-dichloropyrimidine is selectively reacted under Suzuki coupling conditions. Is there any way where this regioselectivity of the coupling can be predicted?

Suzuki coupling scheme

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    $\begingroup$ There are the Handy rules for predicting regioselectivity of cross-coupling for polyhalogenated heterocycles, based on the 1H NMR shifts, but for pyrimidine there is a general preference for cross-coupling at C-4 and C-6 which runs contrary to the Handy predictions. See also Baran group meeting on heterocycle haloselectivity $\endgroup$ – orthocresol Aug 17 '17 at 15:33

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