5305-59-9

Pale Yellow Solid

4-Amino-6-chloropyrimidine is an intermediate of sulfa-6-methoxypyrimidine.

4-Amino-6-chloropyrimidine has been shown to inhibit the proliferation of cancer cells in vitro and in vivo, without affecting normal cells. 4-Amino-6-chloropyrimidine also inhibits kinase activity and protein synthesis in cancer cells. This drug has a potent inhibitory effect on cell proliferation. 

The general procedure for the synthesis of 4-amino-6-chloropyrimidine from 4,6-dichloropyrimidine was as follows: to a suspension of 4,6-dichloropyrimidine (3.0 g, 20 mmol) in isopropanol (40 mL) was slowly added the appropriate amine, with the rate of addition being controlled so as to maintain the internal temperature of the reaction system at no more than 40°C. The reaction mixture was stirred continuously for 1 hour at 25°C. After addition, the reaction mixture was stirred continuously at 25 °C for 1 hour. Upon completion of the reaction, water (30 mL) was added and the resulting suspension was cooled to 0 °C in an ice bath. The precipitated product was collected by filtration and washed sequentially with pre-cooled isopropanol/water solvent mixture (V/V=2:1, 50 mL) and pure water. Finally, the resulting solid product was dried under vacuum to obtain the target compound 4-amino-6-chloropyrimidine.

[1] Journal of Medicinal Chemistry, 2011, vol. 54, # 20, p. 7066 - 7083
[2] European Journal of Medicinal Chemistry, 2014, vol. 75, p. 11 - 20
[3] Patent: WO2012/35039, 2012, A1. Location in patent: Page/Page column 84
[4] Patent: US2012/15943, 2012, A1. Location in patent: Page/Page column 54
[5] ChemMedChem, 2017, vol. 12, # 16, p. 1390 - 1398