Methylation of Thiouracils and Thioxanthines with Trimethyl Phosphate

Abstract Preparation of alkyl derivatives of thiouracils and thioxanthines has been carried out by ring cyclization1 and sulfurization of alkyl derivatives of uracil and xanthines with phosphorus pentasulfide.2–4 However, direct alkylation of thiouracils and thioxanthines has been described by a limited number of papers using dimethyl sulfate,5,6 methyl iodide,7,8 etc. Previously we reported that trimethyl phosphate (TMP) was useful for N-methylation of various azaaromatics.9 In view of the recent biological interest on methyl derivatives of natural products,10 we wish to communicate here the reactions of thiouracils and thioxanthines with TMP.