Regards.
Needs to develop the synthesis of a particular compound and a intermediate includes in its structure a 12C hydrocarbon chain separating two pyrimidine rings. This compound is a insoluble solid in heptane, hexane, DMF, DMSO, chloroform. Can somebody suggest a solvent for this case? if possible using a solvent structurally simple to use as NMR-Solvent?
what exactly your compound ? you can check it with proper solvent interaction . Try to used the mixed solvent ratio ingredient. start with n-pentane , ethyl acetate ,Isopropanol .
all solvent that you used are slightly polar, in this case you may need to increase the relative polarity you can use MeOH or other alcohol?
I am not sure about the structure of your compound, but from what you have described I feel it should be soluble in acetone. You can also record the NMR spectrum of it in acetone-d6.
All the best.
Poor solubility in the solvents described doesn't leave much. Try D6-benzene, D4-methanol and D4-acetic acid to complete the orthogonal set. Adding trifluoroacetic acid to your mixture may help solubilise your pyrimidine rings as the protonated salt and is structurally easy to account for by NMR.
If you have a real pyrimidine, not an uracil or hydroxypyrimidine, TFA-D2O should work, as pyrimidine is slightly basic. But if you have an uracil derivate - those usually cause solubility problems - you can use D2O-NaOH, uracil is somewhat acidic, pK is ca. 10.
Also adding just some drop of d-TFA to the dispersion in d-DMSO might do the trick
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