Acetic Acid → 4-Amino-3,6-dimethyl-2-(3-pyridinyl)thieno[2,3-b]pyridine-5-carboxylic acid

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Reaction Conditions

Reaction Steps

A mixture of ethyl 4-amino-3,6-dimethyl-2-(3-pyridinyl)thieno[2,3-b]pyridine-5-carboxylate (120 mg, 0.367 mmol) (Description 32) in DMSO (3 mL) and 2M NaOH (0.916 mL, 1.833 mmol) was heated at 120° C. for 1 h. After cooling to RT, the mixture was diluted with water (20 mL), acidified with acetic acid to pH 6. The mixture was extracted with 10% MeOH in DCM (5×30 mL). The combined organics were dried and concentrated. The residue was passed through a C18 solid phase extractor cartridge, eluted with water (4×30 mL) followed by MeOH (4×30 mL). The combined organics were concentrated and dried at 55° C. in a vacuum oven, to afford the title compound (98 mg). LCMS (A) m/z: 300 [M+1]+, Rt 0.58 min (acidic).

Provenance & Evidence