Conversion of Simple Pyrimidines into Derivatives with a Carbon Functional Group

The synthesis of pyrimidine derivatives bearing carbon functional groups, such as CH20H, CHO, COR (or COAr), CN, CONR2, and COOR, at the 2-or 4-position is described.The most practical and experimentally simplistic methods for the preparation of these pyrimidines are concluded to be as follows.Hydroxymethylpyrimidines are best prepared by direct hydroxlmethylation of pyrimidines with a free 2-or 4-position using hydroxymethyl radical.Pyrimidinealdehydes are readily obtained by oxidation of methylpyrimidines with a limited amount of selenium dioxide.It is recommended that acylpyrimidines are prepared from the corresponding nitriles by Grignard reaction.In some cases homolytic acylation, rather than the above method, can be used for their preparation.The synthesis of pyrimidinecarboxylic acids and related compounds is described together with the interconversion of nitriles.amides, and esters.In addition, selectivity of reactions on the pyrimidine ring occasionally observed during our investigations is discussed briefly in the last chapter of this paper.