Sugar Esters of Nitrogenous Fatty Acids

Abstract

Hitherto, activated methyl groups attached to heterocycles other than quaternary bases could not be formylated (see, for example [ 1 I).Arnolil recently reported the reaction of y-picoline with dimethylformamide/acid chloride complexes to give (4pyridyl)malondialdehyde [2]. We have obtained (4-pyrimidy1)malondialdehyde (3) by the reaction o f 4-methylpyrimidine (I) with 2 moles of diniethylformamide/phosgene complex (Z), and subsequent hydrolqsis. I n contrast to the reaction of y-picoline, however, the monoformylation product, vir. 4-($-dimethylaminovinyl)pyrimidine (4), was also successfully obtained in 80 :4 yield from the reaction of ( I ) with (2) in the presence of molar quantities of HCI. Compound (4) is also formed in 70 % yield from ( I ) and dimethylformamide diethylacetal. ----CH3 C1 CKa Br CsH5 C1 GHs C I GHs Br GH5