Dimethylformamide → 6-aminopyrimidine-4-carbonitrile

Participants

Reaction Conditions

Reaction Steps

A mixture of 6-chloropyrimidin-4-amine (3.0 g, 23 mmol), zinc (II) cyanide (5.4 g, 46 mmol) and tetrakis(triphenylphosphine)palladium(0) (1.3 g, 1.2 mmol) in dry DMF (50 mL) was heated to 120° C. under nitrogen atmosphere for 15 hours. EtOAc (100 mL) was added and the insoluble precipitate was removed by filtration. The filtrate was diluted with water (100 mL), and extracted with EtOAc (3×50 mL). The combined organic extract was washed with brine, dried over Na2SO4, and concentrated under reduced pressure. The residue was purified by reverse phase column chromatography, eluting with a 0-60% gradient of CH3CN in 0.5% NH4HCO3 to give the desired product as a pale yellow solid (0.6 g, 21% yield). LCMS (ESI) m/z: 121.2 [M+H+].

Provenance & Evidence