2-(Dimethylamino)ethanol → HCID 118037497, compound

Participants

Reaction Steps

2-(dimethylamino)ethanol (0.293 ml, 2.92 mmol) was treated at room temperature with KHMDS (1 M in THF, 2.19 ml, 2.19 mmol). The reaction mixture was stirred for 2 min and then added to a solution of 6-amino-4-fluoronicotinonitrile (intermediate 21, 100 mg, 0.729 mmol) in THF (2 ml). The resulting dark brown solution was stirred at room temperature for 60 min, quenched with sat. aq. NH4Cl, directly absorbed on isolate and dried under vacuum. The crude material was purified by reverse phase chromatography (13 g C18 cartridge, 0.1% TFA in water/acetonitrile 100:0 to 0:100). The product containing fractions were concentrated. The residue was treated with a small amount sat. aq. NaHCO3 and NaCl (s) and extracted with CH2Cl2 (5×). The combined organic layers were dried over Na2SO4 and concentrated to give the title compound as a white solid. (UPLC-MS 3) tR 0.45 min; ESI-MS 207.2 [M+H]+.

Provenance & Evidence