Shan Hou, C. Chen, Ping Wang
Mar 1, 2016
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Abstract
The pyrimidine compounds are a class of nitrogen-containing heterocyclic compounds. 5-(4-bromophenyl)-4, 6-dichloropyrimidine is an important intermediate in the synthesis of pyrimidines, dimethyl2-(4-bromophenyl) malonate and 5-(4-bromophenyl) pyrimidine-4,6-diol are important intermediates in compound 1. In this work, a rapid synthetic method for compound 1 was established. The compound 1 was synthesized from the commercially available methyl 2-(4-bromophenyl) acetate through three steps. The structure was confirmed by MS and 1HNMR. Furthermore, the synthetic method was optimized. The total yield of the three steps was 52.8% (calculated from methyl 2-(4-bromophenyl) acetate). Introduction 5 (4-Bromophenyl)-4, 6dichloropyrimidine (1) is a key intermediate and has a wide range of applications in the pharmaceutical and chemical fields. N ( 5 ( 4 – bromophenyl ) – 6 – chloropyrimidin – 4 –y l ) butane-1sulfonamide [1] (2) was designed and synthesized basing on 5-(4-bromophenyl)-4, 6-dichloropyrimidine. 5-(4-bromophenyl)-4-(2-((5-bromopyrazin-2-yl) oxy) ethoxy) -6-chloropyrimidine [2] (3) was synthesized according to 5( 4 –bromophenyl )-4, 6-dichloropyrimidine. Bolli M, Boss C, Clozel M [3] et al. used 5( 4bromophenyl )-4, 6-dichloropyrimidine as a key intermediate to synthesize 1( 5 ( 4 – bromopheny l) 6chloropyrimidin -4yl ) N ( 2methoxyethyl ) methanesulfonamide (4). The structures of representative compounds were shown in Fig. 1 As have been reported, 5-(4-bromophenyl)-4, 6-dichloropyrimidine was an important intermediate for synthesis those active compounds. Matulenko M A, PaIght E S, Frey RR, et al make 5-(4-bromophenyl)-4, 6-dichloropyrimidine in good yields. CuccIa S J [6] and K hetrapal C L [7] synthesized some similar compounds. In this paper, we summarized and optimized the above methods and the synthetic methods reported in the literature. Using methyl 2-(4-bromophenyl) acetate to synthesize dimethyl 2-(4-bromophenyl) malonate, then synthesize 5-(4-Bromophenyl) pyrimidine-4, 6-diol and 5-(4-bromophenyl)-4, 6-dichloropyrimidine. 4th International Conference on Machinery, Materials and Computing Technology (ICMMCT 2016) © 2016. The authors Published by Atlantis Press 773