Hydrochloric Acid → 4-{2-[(2-Aminoethyl)amino]-5-imidazolylpyrimidin-4-yl}benzenecarbonitrile

Participants

Reaction Steps

Aqueous 3M HCl (15-30 ml) was added to a stirred solution of (tert-butoxy)-N-(2-{[4-(4-cyanophenyl)-5-imidazolylpyrimidin-2-yl]amino}ethyl)carboxamide (0.15 M) in CH3CN (50 ml) at room temperature until the reaction became slightly turbid. After 16 hours, the reaction was partitioned between dichloromethane (200 ml) and 1M HCl (200 ml). The layers were separated, and the aqueous layer was extracted with dichloromethane (3×200 ml). The aqueous layer was basified carefully with solid NaHCO3 to pH 7-8. A solid forms which can be filtered and dissolved in CH3CN (100 ml). The organic solution is washed with sat. aq. NaHCO3 (50 ml), brine (50 ml), dried with Na2SO4, filtered, and concentrated. The crude product was purified by flash chromatography over silica gel. The column was eluted first with a 1:1 mixture of dichloromethane/methanol followed by a mixture of 5% TEA/10% water/85% methanol to elute the product. The proper fractions were condensed. The dark yellow glass was dried overnight in vacuo giving 4-{2-[(2-aminoethyl)amino]-5-imidazolylpyrimidin-4-yl}benzenecarbonitrile in 89% yield.

Provenance & Evidence