2-Bromopyrimidine → 3-[4-(2-Pyrimidinyl)phenyl]-2-propyn-1-ol

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Reaction Steps

A mixture of 2-bromopyrimidine (1.00 g, 6.29 mmol) and Pd(Ph3P)4 (220 mg, 0.19 mmol) in ethylene glycol dimethyl ether (25 mL) was stirred for 10 min, a slurry of sodium bicarbonate (1.58 g, 18.81 mmol) and [4-(3-hydroxy-1-propynyl)phenyl]boronic acid (1.32 g, 7.50 mmol, prepared as described in Reference Example 235) in water (25 mL) was added, and the mixture was heated to reflux for 4 h. The cooled reaction mixture was diluted with methylene chloride (100 mL) and washed with water (100 mL). The aqueous layer was extracted with dichloromethane (25 mL) and the combined organic layers were dried (MgSO4) and concentrated. Purification by chromatography (SiO2, 3:2 hexane/ethyl acetate) provided 1.04 g (79%) of the title compound as a yellow solid. MS 211 (M+H)+.

Provenance & Evidence