Benzyl Alcohol → 3-Amino-6-benzyloxy-5-chloro-4-methyl-thieno[2,3-b]pyridine-2-carboxylic acid cyclopropylamide

Participants

Reaction Conditions

Reaction Steps

To a solution of benzyl alcohol (0.541 g, 5.00 mmol) in THF (2.5 ml) at room temperature is added dropwise a solution of lithium bis(trimethylsilyl)amide (1.0 M in hexanes)(2.50 ml, 2.50 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 (0.345 g, 1.00 mmol). The reaction mixture is heated at 80° C. in a sealed tube for 2 hours, cooled to room temperature, and then quenched by the addition of water (15 ml). The mixture is diluted to 100 ml with water and then cooled to 0° C. and stirred. A yellow precipitate is formed. This solid is collected by filtration and purified by flash chromatography (1.5:1 hexane:EtOAc) to give the title compound as a pale yellow solid (0.130 g, 33%). Mass (m/z): 388.2 (M++1), 386.2 (M+−1).

Provenance & Evidence