Diisopropylethylamine → HCID 11584219, compound

Participants

Reaction Steps

5-(3,4-Dimethoxy-phenyl)-pyrimidine-2-thiol 1f (0.75 g, 3 mmol) was added to a solution of the 2-chloroacetamide 1d (1.3 g, ˜80% purity, ˜3.6 mmol, obtained from step 3) and diisopropylethylamine (0.78 mL, 4.5 mmol, 1.5 equiv) in dry CH2Cl2. The resulting suspension was stirred at rt for about 2 h, at which time the reaction mixture became a dark brown solution and all the solid disappeared. The mixture was then concentrated and chromatographed on silica gel (ethyl acetate). The fractions containing the major product were combined and concentrated to an oily residue. Trituration of the oil with ether afforded 3-({2-[5-(3,4-dimethoxy-phenyl)-pyrimidin-2-ylsulfanyl]-acetylamino}-methyl)-piperidine-1-carboxylic acid tert-butyl ester 1g (0.83 g, 55%) as a dark brown solid.

Provenance & Evidence