Ammonium Hydroxide → 2-Chloro-5-phenylthieno[2,3-d]pyrimidine

Participants

Reaction Steps

2,4-Dichloro-5-phenyl-thieno[2,3-d]pyrimidine (1 g, 3.56 mmol) and zinc dust (2.34 g, 35.6 mmol) were combined and stirred in ethanol (10 mL). NH4OH (1 mL) was added and the reaction heated to reflux for 2 hours. The reaction mixture was allowed to cool to room temperature, diluted with ethyl acetate (50 mL) and filtered through celite. The filtrate was washed with water (100 mL), dried over Na2SO4 and concentrated at reduced pressure. The resulting residue was purified by flash chromatography, eluting with a gradient of petroleum ether to 90/10 petroleum ether/ethyl acetate to afford 2-chloro-5-phenyl-thieno[2,3-d]pyrimidine (260 mg).

Provenance & Evidence