2,5-Dihydroxymethyl-4-methoxy-3-methylpyridine is a substituted pyridine derivative featuring two hydroxymethyl groups at the 2- and 5-positions, a methoxy substituent at position 4, and a methyl group at position 3. The molecule exhibits a rigid aromatic heterocyclic core with electron-donating methoxy and methyl groups, while the hydroxymethyl functionalities introduce steric bulk and potential hydrogen-bonding capacity. This compound arises as a process-related impurity during the synthesis of pyridine-based APIs, likely due to competing alkylation and hydroxylation pathways. Its distinct substitution pattern enables use as an HPLC reference standard for impurity profiling in parent drug manufacturing.
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InChI=1S/C9H13NO3/c1-6-8(5-12)10-3-7(4-11)9(6)13-2/h3,11-12H,4-5H2,1-2H3
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