Methyl 5-aminopyridine-2-carboxylate → (5-Aminopyridin-2-YL)methanol

Participants

Reaction Conditions

Reaction Steps

To a 250 ml three necked round bottom flask was added methyl 5-aminopicolinate (2.0 g) in THF (40 ml) under nitrogen atmosphere and cooled to 0-5° C. After 15 min, 2.0 M solutions of LiAlH4 (19.7 ml) was added under nitrogen atmosphere and allow it to warm up to room temperature and stirred at same temperature for 1 hr. After completion of the reaction, the reaction mixture was cooled to 5° C. and quenched with sat. NH4Cl solution (25 ml) and diluted with water, followed by extraction with ethyl acetate. The combined organics were washed with water, dried over Na2SO4 and evaporated to afford brown oil product. The aqueous layer was concentrated to give residue which was washed with 30% methanol in ethyl acetate. Resultant washing was concentrated to afford brown oil (crude). Both the crude material were combined and subjected for column purification using 8% methanol in chloroform to yield 1.3 g of (5-aminopyridin-2-yl)methanol.

Provenance & Evidence