49845-33-2

Yellow Solid

Intermediate in a solid-phase synthesis of diaminopurines.1

Molecular docking analysis has shown that 2,4-dichloro-5-nitropyrimidine can bind to EGF receptor sites on the surface of tumor cells, thereby inhibiting their growth.

General procedure for the synthesis of 2,4-dichloro-5-nitropyrimidine from 5-nitropyrimidine-2,4(1H,3H)-dione: 5-nitrouracil (6.28 g, 0.040 mol) was mixed with phosphorus triclosan (26 mL), and N,N-dimethylaniline (8 mL) was slowly added under stirring conditions. The reaction mixture was then heated to 110 °C and maintained at this temperature for 8 hours. Upon completion of the reaction, the excess trichlorophosphorus was removed by distillation. The remaining mixture was ground and separated by silica gel column chromatography. Finally, the collected fractions were concentrated to give 6.2 g of yellow oily liquid product in 94% yield.

[1] Patent: CN106432239, 2017, A. Location in patent: Paragraph 0066; 0071; 0072
[2] Journal of Heterocyclic Chemistry, 2012, vol. 49, # 2, p. 321 - 328
[3] Tetrahedron Letters, 2006, vol. 47, # 50, p. 8897 - 8900
[4] Patent: WO2010/83645, 2010, A1. Location in patent: Page/Page column 27
[5] Patent: US7256196, 2007, B1. Location in patent: Page/Page column 8; 9-10