Application
5-Amino-4,6-dichloro-2-methylpyrimidine can be used as an intermediate in medical synthesis, such as the preparation of mosonidine. Mosonidine is a widely used antihypertensive drug.
Synthesis
GENERAL METHOD: 10% Pd/C catalyst (0.05 g) was added to a solution of 4,6-dichloro-2-methyl-5-nitropyrimidine (4.48 mmol) in ethyl acetate (EA, 20 mL) in a Parr hydrogenation reactor. Subsequently, the air in the reactor was replaced with nitrogen three times and the hydrogenation reaction was carried out at room temperature and at atmospheric pressure. Upon completion of the reaction, the Pd/C catalyst was removed by diatomaceous earth filtration and the filtrate was concentrated to afford the intermediate 2-methyl-4,6-dichloro-5-aminopyrimidine (11a). The product was a light-colored solid, yield: 84.0%; mass spectrum (ESI) m/z: 177.94 [M + H]+.
References
[1] European Journal of Medicinal Chemistry, 2017, vol. 140, p. 212 - 228
[2] Chemistry of Heterocyclic Compounds (New York, NY, United States), 1983, p. 1113 - 1115
[3] Khimiya Geterotsiklicheskikh Soedinenii, 1983, vol. 19, # 10, p. 1398 - 1400
[4] Journal of the Chemical Society, 1954, p. 3832,3833
[5] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 17, p. 5721 - 5726
