1,3-Propanediol → 3-Amino-5-chloro-N-cyclopropyl-6-(3-hydroxypropoxy)-4-methylthieno[2,3-b]pyridine-2-carboxamide

Participants

Reaction Conditions

Reaction Steps

To a solution of 1,3-propanediol (1.053 g, 13.84 mmol) in THF (3 ml) at room temperature is added dropwise a solution of lithium bis(trimethylsilyl)amide (1.0 M in hexanes) (3.50 ml, 3.50 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 75° C. for 1 hour, cooled to room temperature, and then quenched by the addition of water (15 ml). Ice is added to the reaction mixture and, while stirring, a yellow precipitate is formed. This solid is collected by filtration and placed in the vacuum oven to dry (60° C. for 16 hours). This affords the title compound as a yellow solid (0.240 g, 67%). Mass (m/z): 356.2 (M++1), 354.1 (M+−1).

Provenance & Evidence