Aluminium lithium hydride → HCID 24826586, compound

Participants

Reaction Steps

Ethyl 2-(2-(4-(phenylthio)pyridin-2-ylamino)thiazol-4-yl)acetate (1.20 g, 3.23 mmol) in THF was added to a solution of 1.0 M lithium aluminum hydride (9.69 mL, 9.69 mmol) in ether and THF (50 mL) at 0° C. The reaction mixture was stirred for 40 minutes, and cooled while carefully quenching with an excess of sodium sulfate decahydrate. A small amount of anhydrous magnesium sulfate was added and the reaction mixture was stirred overnight. The reaction mixture was filtered, and the cake was washed with THF several times. The combined filtrates were concentrated and the residue was recrystallized from 3:1 ethyl acetate:hexanes (50 mL). The crystals were filtered, washed with hexanes and dried to afford 2-(2-(4-(phenylthio)pyridin-2-ylamino)thiazol-4-yl)ethanol (0.501 g, 47.1% yield) as light pink crystals/needles. 1H NMR (d6-DMSO) δ 11.11 (s, 1H), 8.08 (d, 1H), 7.53-7.61 (t, 6H), 6.73 (s, 1H), 6.57 (s, 1H), 6.56 (m, 1H), 4.58 (t, 1H), 3.65 (m, 2H), 2.69 (t, 2H).

Provenance & Evidence