METHYL-6-HYDROXYMETHYL-2-CARBOXYLATE PYRIDINE

Chemical properties

White or off-white solid

The Uses of METHYL-6-HYDROXYMETHYL-2-CARBOXYLATE PYRIDINE

Methyl 6-(Hydroxymethyl)-2-pyridinecarboxylate is a chemical compound used in the synthesis of Losartan (L470500) derivatives as AT1 antagonists in the preparation of antihypertensive agents. Also used to prepare telomerase inhibitors for in vivo inhibitory activity.

Synthesis

Into a 100-mL round-bottom flask, was placed a solution of 2,6-dimethyl pyridine-2,6- dicarboxylate (950 mg, 4.87 mmol, 1.00 equiv) in a solvent mixture of methanol (33.2 mL) and dichloromethane (14.2 mL). NaB (185 mg, 5.02 mmol, 1.00 equiv) was added to the reaction mixture in several batches at 0°C. The resulting solution was stirred overnight at room temperature, and then it was quenched by the addition of 50 mL of NC1 (aq.). The resulting solution was extracted with 2x50 mL of dichloromethane and the combined organic layers were dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1 : 1-2: 1) as eluent to yield 750 mg (92%) of methyl 6-(hydroxymethyl)pyridine-2-carboxylate as a white solid.