Sodium Iodide → HCID 86593416, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of [1-(2-hydroxyethyl)-5-(tritylamino)-1H-pyrazol-4-yl]formamide (2 g) in N,N-dimethylformamide (30 ml) was added sodium hydride (213 mg, 60% oil suspension) under a nitrogen stream at, 0° C., and the whole mixture was stirred at 0° C. for 20 minutes. A solution of tert-butyl (3-bromopropyl)carbamate (1.27 g) in N,N-dimethylformamide (10 ml) and sodium iodide (799 mg) were added to the above solution, and the mixture was stirred overnight. 10% Aqueous potassium hydrogen sulfate solution (5 ml) was added, and the whole mixture was extracted with ethyl acetate. The extract was washed with water and brine and dried over magnesium sulfate. Evaporation of the solvent under reduced pressure gave an oil, which was chromatographed on silica gel eluting with dichloromethane-ethyl acetate (2:1) to give tert-butyl (3-{N-formyl-N-[1-(2-hydroxyethyl)-5-(tritylamino)-1H-pyrazol-4-yl]amino}propyl)carbamate (1 g). The NMR spectrum of this compound indicates the existence of its rotamer.

Provenance & Evidence