In an attempt to prepare 6-anilino and 6-benzylaminopteridines, 2,4,7-triamino-6-methylsulfonyl and 2,4,7-triamino-6-methylsulfinylpteridines were prepared and reacted with a number of benzylamines and aniline. These hard nucleophiles gave amine exchange products with no displacement at the 6 position. Aliphatic amines gave exchange in the 2,4-and 7-positions. The exchange occurring in the 7-position must be occurring by an AE mechanism. This is the first such exchange reported in a ring other than a 1,3-azine. Aniline gave no exchange product except in an acid catalyzed reaction, and then gave exchange in only the 2 and 4-positions. Numerous reactions on related substrates, are reported. Soft nucleophiles, thiophenols, gave displacement on the same substrates in the 6-position only. Three new pteridine 5-oxides were prepared. One of these was prepared by a new synthetic route using an intramolecular cyclization of a 5-nitropyrimidine. The following subjects are reviewed: amine exchanges, displacement of alkylsulfonyl and alkylsulfinyl moieties in azines, and 6-aminopteridines.
College and Department
Chemistry and Biochemistry
BYU ScholarsArchive Citation
Johnston, William David, "The attack of hard and soft nucleophiles on 6-methylsulfonyl-, 6-methylsulfinyl-, and 6-methylthioaminopteridines" (1974). Theses and Dissertations. 8247.