Tetrahydrofuran → 2-Aminopyridine-4-carbothioamide

Temperature

60 °C

A mixture of 2-aminopyridine-4-carbonitrile (6.0 g, 50 mmol), O,O′-diethyl dithiophosphate (11 mL, 60 mmol), tetrahydrofuran (25 mL) and water (25 mL) was stirred at 60° C. for 4 hr. To the reaction mixture was added O,O′-diethyl dithiophosphate (2.8 mL, 15 mmol) and the mixture was stirred at 60° C. for 1 day. To the reaction mixture was added aqueous sodium bicarbonate solution, and the mixture was extracted with ethyl acetate. The combined organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate, and the insoluble material was filtered off. The filtrate was concentrated under reduced pressure, and the obtained residue was washed with diisopropyl ether to give the title compound (6.2 g, 81%) as a yellow solid.

1. stirringthe mixture was stirred at 60° C. for 1 day
2. extractionthe mixture was extracted with ethyl acetate
3. washThe combined organic layer was washed with saturated brine
4. dry with materialdried over anhydrous magnesium sulfate
5. filtrationthe insoluble material was filtered off
6. concentrationThe filtrate was concentrated under reduced pressure
7. washthe obtained residue was washed with diisopropyl ether

ORD record

ord-b6ca5242bd964e52875f2137b1e320ce

Source dataset

uspto-grants-2015_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09139589B2