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Synthesis of 2-amino-4,6-dimethoxypyrimidine with dimethyl carbonate as methylating agent

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Abstract

2-amino-4,6-dimethoxypyrimidine (ADM) was prepared from 2-amino-4,6-dihydroxypyrimidine (ADH) in the presence of potassium carbonate and phase transfer catalyst (PTC), with dimethyl carbonate (DMC) instead of conventional toxic reagents (such as haloalkane and dimethyl sulfate, etc.). The best conversion (87.7 %) of ADH and selectivity (40.5 %) toward ADM were achieved under optimized conditions: tetrabutyl ammonium bromide (TBAB) as PTC, n(ADH):n(DMC):n(TBAB):n(K2CO3) = 1:5:0.1:3, reaction time = 10 h and reaction temperature = 150 °C.

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Acknowledgments

The authors are grateful for the financial support from the National Basic Research Program of China (973 Program) (Grants 2010CB732206 and 2012CB215306) and the National Natural Science Foundation of China (No.21276050).

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Authors and Affiliations

  1. School of Chemistry and Chemical Engineering, Southeast University, Nanjing, 210094, People’s Republic of China

    Zhen Xiong, Minghao Zhou & Guomin Xiao

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  1. Zhen Xiong
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  2. Minghao Zhou
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  3. Guomin Xiao
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Correspondence to Guomin Xiao.

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Xiong, Z., Zhou, M. & Xiao, G. Synthesis of 2-amino-4,6-dimethoxypyrimidine with dimethyl carbonate as methylating agent. Res Chem Intermed 40, 1789–1797 (2014). https://doi.org/10.1007/s11164-013-1082-7

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  • DOI: https://doi.org/10.1007/s11164-013-1082-7

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