Methanol → HCID 70035325, compound

Participants

Reaction Steps

A solution of 0.24 (0.4 mmol) (2S,4R)-2-Chloro-4-[2-(2,4,5-trifluoro-benzyloxymethyl)-4-tritylsulfanyl-pyrrolidin-1-yl]-pyrimidine in 8 ml DMF was treated at 0° C. with 0.05 ml (1.2 mmol) MeOH and 0.054 g (1.24 mmol) 55% NaH. The reaction was kept at this temperature (6 h) and warmed up over night to RT. After extraction with aqueous saturated NH4Cl/Et2O (3×), the organic phases were washed with aq. 10% NaCl, dried (Na2SO4) and evaporated. Flash chromatography (CH2Cl2 EtOAc 95:5) gave 0.14 g (54%) (2S,4R)-4-[2-(2,5-Difluoro-4-methoxy-benzyloxymethyl)-4-tritylsulfanyl-pyrrolidin-1-yl]-2-methoxy-pyrimidine, MS: 640 (MH+). TFA/triisopropylsilane deprotection, (see General method for S-deprotection, Method D) gave (3R,5S)-5-(2,5-Difluoro-4-methoxy-benzyloxymethyl)-1-(2-methoxy-pyrimidin-4-yl)-pyrrolidine-3-thiol, MS: 398 (MH+).

Provenance & Evidence