Methyl 6-aminopyridine-2-carboxylate → 6-Amino-2-pyridinemethanol

Temperature

0 °C

6-Amino-pyridine-2-carboxylic acid methyl ester (6-1, Kelly, T. R.; Lang, F. J. Org. Chem. 1996, 61, 4623-4633) 2.37 g (15.6 mmol) was dissolved in 16 mL anhydrous THF and the resulting solution was cooled to 0° C. LAH (15.6 mL of a 1M solution) was added slowly. An additional 8 mL of THF was added during the addition of LAH to keep the mixture from becoming too viscous. After 3 h the reaction was quenched by the sequential addition of 0.59 mL water, 0.59 mL 15% NaOH (aq), and 1.77 mL water. After stirring for 1 h the mixture was filtered through a plug of celite, washing with THF. The filtrate was concentrated to afford 1.6 g of a yellow oil. Purification by flash column chromatography (eluting with a gradient of CH2Cl2 to 90:10 CH2Cl2/MeOH) afforded the titled compound as a white solid. 1H NMR(CDCl3): δ 7.42 (t, 1H, J=7.6 Hz), 6.60 (d, 1H, J=7.7 Hz), 6.41 (d, 1H, J=7.5 Hz), 4.59 (s, 2H), 4.52 (bs, 2H).

1. customAfter 3 h the reaction was quenched by the sequential addition of 0.59 mL water, 0.59 mL 15% NaOH (aq), and 1.77 mL water
2. filtrationwas filtered through a plug of celite
3. washwashing with THF
4. concentrationThe filtrate was concentrated

ORD record

ord-728727ab1cda490ba47734bacf3f9662

Source dataset

uspto-grants-2003_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06586424B2