A novel approach to the synthesis of 6-substituted uracils in three-step, one-pot reactions

JI Bardagi, RA Rossi

Index: Bardagi, Javier I.; Rossi, Roberto A. Journal of Organic Chemistry, 2008 , vol. 73, # 12 p. 4491 - 4495

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Citation Number: 15

Abstract

From the commercial 6-chloro-2, 4-dimethoxypyrimidine (1) and by a photostimulated reaction with Me3Sn− ions, 2, 4-dimethoxy-6-(trimethylstannyl) pyrimidine (2) was obtained in 95% yield. By the cross-coupling reaction of 2 with 1-iodonaphthalene as electrophile catalyzed by Pd (Stille reaction), 2, 4-dimethoxy-6-(naphthalen-1-yl) pyrimidine (9) was obtained in 76% yield. By hydrolysis of 9, 6-(1-naphthyl) uracil was obtained in 98% of ...