Pyrimidine Derivatives. V. Synthesis and Nucleophilic Reactions of 5-Bromo-6-bromomethy1-1-(2-bromoethyl and 2-bromopropy1)-3-methyl-2, 4 (1H, 3H)-pyrimidinedione

Abstract

The reaction of 1-(2-hydroxyethyl and 2-hydroxypropy1)-3, 6-dimethyl-2, 4 (1H, 3H)-pyrimidinedione (2 and 3) with bromine afforded 5-bromo-6-bromomethyl-l-(2-bromoethyl and 2-bromopropy1)-(4 and 5), 5-bromo-1-(2-bromoethyl)-6-dibromomethy1-2, 4 (1H, 3H)-pyrimidinedione (6), and 8, 8-dibromo-6, 8a-dimethyl (or 2, 6, 8a-trimethyl)-5, 7-dioxoperhydrooxazolo [3, 2-c] pyrimidine (8 or 9).
Compound 4 reacted with sodium methoxide to give the 5-debrominated compounds 10, 11, and 13 [1-(2-bromoethyl)-, 1-vinyl-, and 1-(2-hydroxyethyl)-6-bismethoxy) methy1-3-methy1-2, 4-(1H, 3H)-pyrimidinedione]. Treatment of 4 with sodium dithiocarbamate and potassium thiolacetate gave 1 [2-(N, N-dimethylthiocarbamoylthio) ethy1]-6-(N, N-dimethylthiocarbamoylthiomethy1)-and 1-(2-acetylthioethyl)-6-acetylthiomethy1-5-bromo-3-methy1-2, 4 (1H, 3H)-pyrimidinedione (14 and 15).
The reaction of 4 with sodium benzenesulfinate yielded 5-bromo-1-(2-bromoethyl)-3-methy1-6-benzenesulfonylmethy1-2, 4 (1H, 3H)-pyrimidinedione or 4-bromo-2-methy1-5-benzenesulfonyl-1, 3 (2H, 8H)-dioxoperhydropyrrolo [1, 2-c] pyrimidine (19 or 21).