Methyl 2-aminopyridine-4-carboxylate → (2-Aminopyridin-4-yl)methanol

Temperature

-45 °C

2-Amino-isonicotinic acid methyl ester (6.0 g, 39.4 mmol) was dissolved in 80 mL anhydrous THF in a flame dried round bottom flask under nitrogen gas. The solution was cooled to −45° C. and LAH (39.4 mL, 1M in THF) was added slowly. The reaction was allowed to warm to 0° C. and was quenched by the addition of 15 mL of 1M NaOH (aq). The solution was filtered and the solid was washed with THF. The filtrate was concentrated to afford the pure product. 1H NMR (DMSO-d6) δ7.79 (d, 1H, J=5.2 Hz), 6.41 (s, 1H), 6.38 (d, 1H, J=5.9 Hz), 5.79 (bs, 2H), 5.19 (t, 2H, J=5.7), 4.35 (d, 2H, J=5.6 Hz).

1. customdried round bottom flask under nitrogen gas
2. additionLAH (39.4 mL, 1M in THF) was added slowly
3. temperatureto warm to 0° C.
4. customwas quenched by the addition of 15 mL of 1M NaOH (aq)
5. filtrationThe solution was filtered
6. washthe solid was washed with THF
7. concentrationThe filtrate was concentrated
8. customto afford the pure product

ORD record

ord-9b4b3fb202ef4fc1aaf222f06e44f3e4

Source dataset

uspto-grants-2003_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06586423B2