Sodium Acetate → HCID 86636265, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of tert-butyl {2-[(E)-2-(5-aminopyridin-3-yl)vinyl]-4-[(2,5-dichloropyrimidin-4-yl)amino]benzyl}carbamate (90.0 mg, 0.185 mmol) in THF (4 mL) was added p-toluenesulfonylhydrazide (0.515 g, 2.76 mmol). The reaction solution was heated to reflux at 90° C., then a solution of sodium acetate (0.363 g, 4.42 mmol) in water (3.7 mL, 20 mmol) was added dropwise over 4 h period. Another portion of p-toluenesulfonylhydrazide (0.343 g, 1.84 mmol) was added to reaction flask, then a solution of sodium acetate (0.242 g, 2.95 mmol) in water was added dropwise overnight under reflux. The reaction solution was diluted with ethyl acetate. Aqueous layer was extracted with ethyl acetate twice. The combined organic solutions were washed with brine, dried over Na2SO4, filtered and concentrated. The residue was purified by flash column chromatography to yield the desired product (56 mg, 62%). LCMS for C24H29Cl2N6O2 (M+H)+: m/z=503.3, 505.3.

Provenance & Evidence