Dichloromethane → 2-Amino-6-hydroxymethyl-pyridine-3-carbaldehyde

Temperature

0 °C

To a mixture of 2-amino-6-methoxymethyl-pyridine-3-carbaldehyde (57 mg, 0.34 mmol) described in Manufacturing Example 26-1-6 and dichloromethane (2 mL) was added boron tribromide (1.0 mL, 1 M dichloromethane solution, 1.0 mmol) at −78° C., which was stirred for 1 hour at 0° C. The reaction mixture was cooled to −78° C., methanol was added at the same temperature, and the excess reagent was quenched. The reaction mixture was gradually allowed to room temperature and was neutralized by adding an ammonium aqueous solution (28%). Water was added to the reaction mixture, which was extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium chloride, and was concentrated under a reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:heptane=4:1) to obtain the title compound (18 mg, 34%).

1. temperatureThe reaction mixture was cooled to −78° C.
2. customthe excess reagent was quenched
3. customwas gradually allowed to room temperature
4. additionby adding an ammonium aqueous solution (28%)
5. additionWater was added to the reaction mixture, which
6. extractionwas extracted with ethyl acetate
7. washThe organic layer was washed with saturated aqueous sodium chloride
8. concentrationwas concentrated under a reduced pressure
9. customThe residue was purified by silica gel column chromatography (ethyl acetate:heptane=4:1)

ORD record

ord-456d5e03b8c844b4a0b6b4bd9857c884

Source dataset

uspto-grants-2012_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08158657B2