REGIOSELECTIVE ALLYLATION AND PROPARGYLATION OF PYRIMIDINES

Article abstract of DOI:10.1016/S0040-4020(01)80069-7

Reactions of pyrimidines 1a and 1b with allylic Grignard reagents 3a-f lead to allyldihydropyrimidines 2a-h and 2l-n in very good yields.Dehydrogenation of 2a-d with DDQ furnished excellent yields of allylpyrimidines 1c-f.Propargylation of 1a with 3g and 3h provides propargyl dihydropyrimidines 2g and 2h respectively. 2g can be oxidised with DDQ to 1g.Allylation of 1c and 1i gives 1m and 1n respectively.Reduction of 1f leads to the branched alkyl derivative 1r.