Potassium Cyanide → 5-chloro-4-(5-cyclopropyl-1H-pyrazol-3-ylamino)pyrimidine-2-carbonitrile

Participants

Reaction Conditions

Reaction Steps

A mixture of 2-bromo-5-chloro-N-(5-cyclopropyl-1H-pyrazol-3-yl)pyrimidin-4-amine (3.0 g, 9.54 mmol, 1.0 eq), KCN (1.24 g, 19.07 mmol, 2.0 eq) and 1,4-diazobicyclo[2,2,2]octan (DABCO.6H2O) (4.20 g, 19.07 mmol, 2.0 eq) in DMSO (50 mL) and H2O (10 mL) was stirred at 80° C. for 4 h. The reaction mixture was diluted with H2O (50 mL) and extracted with EtOAc (3×100 mL). The combined organic phases were washed (brine), dried (Na2SO4), filtered and concentrated. The residue was purified by silica gel chromatography (CH2Cl2/MeOH 500:1 to 50:1 as eluent) to afford 5-chloro-4-(5-cyclopropyl-1H-pyrazol-3-ylamino)pyrimidine-2-carbonitrile (1.9 g, 77%) as a solid. LC-MS (m/z)=261.0 [M+H]+.

Provenance & Evidence