4-Methyl-5-(2-hydroxyethyl)thiazole → HCID 57664411, compound

Participants

Reaction Steps

To a solution of 4-methyl-5-thiazole-ethanol (0.375 g, 2.62 mmol) in THF (1 ml) at room temperature is added dropwise a solution of lithium bis(trimethylsilyl)amide (11.0M in hexanes)(1.74 ml, 1.74 mmol). The reaction mixture is stirred for 15 minutes and then is treated with 3-amino-5-chloro-6-methanesulfinyl-4-methyl-thieno[2,3-b]pyridine-2-carboxylic acid cyclopropylamide (0.300 g, 0.872 mmol). The reaction mixture is stirred at room temperature for 18 hours, then quenched by the addition of water (5 ml). The mixture is partitioned between water and EtOAc (40 ml each). Five ml of 1 N HCl is added, and the layers are shaken and separated. The aqueous layer is extracted with EtOAc (50 ml) and the combined organic layers are dried (anhydrous magnesium sulfate), filtered, concentrated, and flashed (1:2 hexane:EtOAc) to give the title compound as a pale yellow solid (0.094 g, 25%). Mass (m/z): 423.1 (M++1), 421.1 (M+−1).

Provenance & Evidence