Sodium hydride → HCID 86648405, compound

Participants

Reaction Steps

A mixture of (2R,4S)-4-(5-bromo-pyrimidin-2-ylamino)-2-ethyl-pyrrolidine-1-carboxylic acid tert-butyl ester (13.0 mmol; 4.84 g), 3,5-bis(trifluoromethyl)benzyl bromide (26.0 mmol; 7.98 g) and sodium hydride (60% dispersion in mineral oil, 39.0 mmol; 1.56 g) in DMF (52 mL) is stirred for 1.5 hours at room temperature under nitrogen. The reaction mixture is quenched with water then saturated ammonium chloride solution. The product is extracted twice with EtOAc. The combined organic layer is washed with brine, dried over MgSO4, filtered, concentrated under reduced pressure. The obtained residue is purified by silica gel column chromatography (eluent: n-hexane/EtOAc) to give (2R,4S)-4-[(3,5-bis-trifluoromethyl-benzyl)-(5-bromo-pyrimidin-2-yl)-amino]-2-ethyl-pyrrolidine-1-carboxylic acid tent-butyl ester (5.57 g, 72%).

Provenance & Evidence