Ethyl Acetate → (2-Anilinopyrimidin-5-yl)methanol

Participants

Reaction Conditions

Reaction Steps

Ethyl 2-(phenylamino)pyrimidine-5-carboxylate (0.590 g, 2.42 mmol) obtained in Step 2 was dissolved in toluene (25 mL). After cooling to −78° C., a 1 mol/L diisobutyl aluminum hydride-toluene solution (7.30 mL, 7.30 mmol) was added to the solution, followed by stirring at −78° C. for 3 hours. The reaction mixture was added with ethyl acetate followed by stirring vigorously at room temperature. The mixture was sequentially washed with water and saturated brine. The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (chloroform:methanol=50:1) to obtain 5-hydroxymethyl-2-(phenylamino)pyrimidine (386 mg, 79%).

Provenance & Evidence