2-Chloropyrimidine → (2S,4R)-2-[2-(2,4,5-Trifluoro-benzyloxymethyl)-4-tritylsulfanyl-pyrrolidin-1-yl]-pyrimidine

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Reaction Conditions

Reaction Steps

A mixture of 2.08 g (4 mmol)(2S,4R)-2-(2,4,5-Trifluoro-benzyloxymethyl)-4-tritylsulfanyl-pyrrolidine, 0.687 g (6 mmol) 2-chloropyrimidine and 1.16 ml (6.8 mmol) N-ethyldiisopropylamine was heated for 3 h at 80° C. The reaction was cooled and partitioned between H2O/Et2O (3×300). The organic phases were washed with aqueous saturated NaHCO3, aqueous 10% NaCl, dried (NaSO4) and evaporated. Flash chromatography on silica gel (CH2Cl2/EtOAc 97.5:2.5) gave 1.7 g (71%) (2S,4R)-2-[2-(2,4,5-Trifluoro-benzyloxymethyl)-4-tritylsulfanyl-pyrrolidin-1-yl]-pyrimidine, MS: 598 (MH+).

Provenance & Evidence