2-{6-[7-(1-Methyl-1-triethylsilanyloxyethyl)imidazo[1,2-alpha]pyrimidin-3-yl]pyridin-2-yl}benzonitrile → 2-{6-[7-(1-Hydroxy-1-methylethyl)imidazo[1,2-alpha]pyrimidin-3-yl]pyridin-2-yl}benzonitrile

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Reaction Steps

To a solution of crude 2-{6-[7-(1-methyl-1-triethylsilanyloxy-ethyl)imidazo[1,2-α]pyrimidin-3-yl]pyridin-2-yl}benzonitrile in ethanol (3 ml) was added 3 drops of concentrated hydrochloric acid and the mixture left to stir at ambient temperature for 18 h. The solvent was evaporated and the residue made basic by the addition of saturated aqueous sodium hydrogencarbonate. The aqueous phase was diluted with water (30 ml) and extracted with ethyl acetate (2×75 ml). The combined organic phase was washed with water (30 ml) and brine (30 ml), dried over anhydrous sodium sulfate, filtered and evaporated to give an orange oil. This oil was purified on silica eluting with dichloromethane (+1% 0.880 ammonia) on a gradient of methanol (1-3%). Collecting the appropriate fractions followed by recrystallisation from ethyl acetate/isohexane gave 2-{6-[7-(1-hydroxy-1-methylethyl)imidazo[1,2-α]pyrimidin-3-yl]pyridin-2-yl}benzonitrile as a white solid: δH (360 MHz, CDCl3) 1.63 (6H, s), 4.52 (1H, s), 7.16 (1H, d, J 7), 7.55-7.62 (2H, m), 7.74-7.96 (5H, m), 8.36 (1H, s), 10.37 (1H, d, J 7); m/z (ES+) 356 (M++H).

Provenance & Evidence