Ammonium Chloride → (2-Chloro-pyrimidin-4-yl)-(5-tert-butyl-isoxazol-3-yl)-amine

Participants

Reaction Conditions

Reaction Steps

To a solution of 5-t-butyl-isoxazol-3-ylamine (10.0 g, 71.33 mmol) in t-BuOH (500 mL) at 20° C. was added NaOt-Bu (17.1 g, 178.3 mmol) in 3 portions over 10 min. The solution turned pale yellow with the appearance of a thick, white precipitate. The mixture was stirred at 20° C. for 1 h, then 2,4-dichloropyrimidine (15.9 g, 107.0 mmol) was added. The mixture was stirred for an additional 90 min. at 20° C., accompanied by the dissolution of the white precipitate and appearance of an orange color. NH4Cl (aq., sat., 100 mL) and H2O (1 L) were added, and the mixture was extracted with CH2Cl2 (3×200 mL). The combined organic layers were washed with H2O (300 mL), brine, and dried with MgSO4 before being filtered and concentrated under reduced pressure. Purification by chromatography of the crude reaction mixture (96:4 CH2Cl2:MeOH) provided the title compound.

Provenance & Evidence