5-(4-Formylphenyl)pyrimidine → (4-Pyrimidin-5-ylphenyl)methanol

Participants

Reaction Steps

To a 100 mL recovery flask was added 4-(5-pyrimidinyl)-benzaldehyde 48 (1.01 g, 5.49 mmol, 1.0 eq.) and CH3OH (30 mL). The resulting suspension was stirred upon which NaBH4 (311 mg, 8.23 mmol, 1.5 eq.) was added. Upon addition of NaBH4 the reaction became homogeneous. After stirring at room temperature for 2 h, the reaction was complete by LC/MS. The reaction mixture was concentrated and diluted with EtOAc upon which it was washed with a succession of water and brine. The aqueous phases were combined and extracted with EtOAc. The organic phases were dried over anhydrous Na2SO4, filtered, and concentrated to give a fine yellow powder that was used in subsequent reactions without further purification (523 mg, 51%).

Provenance & Evidence