Lithium Chloride → 2-(2-Hydroxy-3-phenyl-propylamino)-3-methyl-5-naphthalen-2-yl-6-pyridin-4-yl-3H-pyrimidin-4-one

Participants

Reaction Steps

To a solution of 2-[3-phenyl-2-oxo-propylamino]-3-methyl-5-naphthalen-2-yl-6-pyridin-4-yl-3H-pyrimidin-4-one (123 mg, 0.27 mmol) in THF (5 mL) at −78° C. was added LDA (Aldrich, 2.0 M in THF, 0.4 mL). The mixture was stirred for 1 h. Lithium chloride (30 mg) was added. After 5 minutes, (1S)-(+)-(10-camphorsulfonyl)oxaziridine (200 mg, 0.87 mmol) was added. The mixture was stirred at −78 for 2 hours, and quenched with water (5 mL) and ethyl acetate (80 mL). The solution was washed with brine (3×50 mL), dried, and evaporated. The crude product was purified by preparative TLC (6% MeOH/CH2Cl2). 8 mg (7%) solids. M+1=477.2.

Provenance & Evidence