Primidine Derivatives. V. : Synthesis and Nucleophilic Reactions of 5-Bromo-6-bromomethyl-1-(2-bromoethyl and 2-bromopropyl)-3-methyl-2,4(1H, 3H)-pyrimidinedione

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概要

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• The reaction of 1-(2-hydroxyethyl and 2-hydroxypropyl)-3,6-dimethyl-2,4(1H, 3H)-pyrimidinedione(2 and 3) with bromine afforded 5-bromo-6-bromomethyl-1-(2-bromoethyl and 2-bromopropyl)- (4 and 5), 5-bromo-1-(2-bromoethyl)-6-dibromomethyl-2,4(1H, 3H)-primidinedione (6), and 8,8-dibromo-6,8a-dimethyl (or 2,6,8a-trimethyl)-5,7-dioxoperhydrooxazolo[3,4-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)methyl-3-methyl-2,4-(1H, 3H)-pyrimidinedione]. Treatment of 4 with sodium dithiocarbamate and potassium thiolacetate gave 1-[2-(N, N-dimethylthiocarbamoylthio)ethyl]-6-(N, N-dimethylthiocarbamoylthiomethyl)- and 1-(2-acetylthioethyl)-6-acetylthiomethyl-5-bromo-3-methyl-2,4(1H, 3H)-pyrimidinedione (14 and 15).The reaction of 4 with sodium benzenesulfinate yielded 5-bromo-1-(2-bromoethyl)-3-methyl-6-benzenesulfonylmethyl-2,4(1H, 3H)-pyrimidinedione or 4-bromo-2-methyl-5-benzenesulfonyl-1,3(2H, 8H)-dioxoperhydropyrrolo[1,2-c]pyrimidine (19 or 21).

• 公益社団法人日本薬学会の論文
• 1988-10-25

著者

• 木下 敏夫

  Faculty of Pharmaceutical Sciences, Nagasaki University

• 古川 淳

  Faculty of Pharmaceutical Sciences, Nagasaki University

• 古川 淳

  School Of Pharmaceutical Sciences Nagasaki University

• 木下 敏夫

  School of Pharmaceutical Sciences, Nagasaki University

• 中畑 典子

  Faculty of Pharmaceutical Sciences, Nagasaki University

• 河内 昭子

  Faculty of Pharmaceutical Sciences, Nagasaki University

• 木下 敏夫

  School Of Pharmaceutical Sciences Nagasaki University

• 河内 昭子

  Faculty Of Pharmaceutical Sciences Nagasaki University

• 中畑 典子

  Faculty Of Pharmaceutical Sciences Nagasaki University

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