Sodium Hydroxide → HCID 23512560, compound

Participants

Reaction Steps

To a solution of 0.70 g (2.6 mmol) [5-(2-Chloro-phenyl)-2-methylsulfanyl-pyrimidin-4-yl]-methyl-amine in 4 ml N,N-dimethylformamide 2.6 ml of a 1M solution potassiumhexamethyldisilazide (2.6 mmol) in THF were added at 0°. After 1 h, 0.92 g (2.6 mmol) (2-(3,5-bis-trifluoromethyl-phenyl)-2-methyl-propionyl chloride in 2 ml THF were added and the reaction mixture stirred for 24 hrs. at RT. The reaction mixture was poured onto 50 ml 0.5 N NaOH-solution. After addition of ethyl acetate the phases were separated, the aqueous layer washed twice with 50 ml ethyl acetate. The combined organic layers were dried (Na2SO4), filtered and evaporated. The residue was purified by chromatography (SiO2, CH2Cl2/ethyl acetate 19:1) to give 0.85 g (58%) 2-(3,5-bis-trifluoromethyl-phenyl)-N-[5-(2-chloro-phenyl)-2-methylsulfanyl-pyrimidin-4-yl]-N-methyl-isobutyramide as a white foam, MS (EI): 547 (M+).

Provenance & Evidence