We want to attach pyrimidine on 4-chloro-3-nitrocoumarine, but we are not sure what is best way to do it successfully, what is best to use as solvent(s) (I found that benzene works for pyridine); is it necessary to remove nitro group before attach pyrimidine? If it is how to do it?
I am not sure what you want to do... I think you are not talking about a substitution of the chlorine atom by any nitrogenatom of the pyrimidine, since this is do to low nucleophilicity of these nitrogenatoms, bad leavinggroup and sp2-hybridized carbonatom not possible!!! If you mean a C-C-coupling my suggestion is attahced. First do zincation according to knochel et al. (Angew. Chem. Int Ed., 2007, 46, 7685-7688.) and afterwards cu-mediated coupling or negishi coulping. This might be successful evenso the chloride is still not e good leaving group for such a coupling.
Menny thanks Philipp! Do you think that will work attachment at position 4 (nitrogenatom) in morfolin or piperazin on same coumatine by substitution of the chlorine atom.
No, for sure not! 2-position will be zincated first therefore you need a competely different startegy.
OK! but if I use pyrimidine derivatives such uracil, as we need to attach it at nitrogen atom,as in uridine (in place of ribose- to attach it to coumarine ring).
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