Sodium Hydroxide → HCID 18406865, compound

Temperature

60 °C

To a solution of 1-aminopyridin-2(1H)-iminium-2,4,6-trimethylbenzenesulfonate (1.24 g, 4 mmol) in EtOH (15 mL) was added NaOH (320 mg, 8 mmol). The mixture was heated to 60° C. and stirred for 1 h. Then methyl 2-hydroxyacetate (720 mg, 8 mmol) was added and the mixture was heated to 80° C. and stirred for 3 h. The resulting mixture was cooled to room temperature and concentrated under reduced pressure. The residue was washed with water (10 mL) and extracted with DCM (15 mL×3). The combined organic layers were washed with brine (10 mL), dried over anhydrous sodium sulfate and concentrated under reduced pressure to afford the title compound as a pale yellow solid (350 mg, 59% yield). ESI MS: m/z 150 [M+H]+.

1. temperaturethe mixture was heated to 80° C.
2. stirringstirred for 3 h
3. temperatureThe resulting mixture was cooled to room temperature
4. concentrationconcentrated under reduced pressure
5. washThe residue was washed with water (10 mL)
6. extractionextracted with DCM (15 mL×3)
7. washThe combined organic layers were washed with brine (10 mL)
8. dry with materialdried over anhydrous sodium sulfate
9. concentrationconcentrated under reduced pressure

ORD record

ord-8517c4432e22476dbc1776db77a1041a

Source dataset

uspto-grants-2014_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08765760B2