4-Aminopyridine → 4-(2,2,2-Trimethylacetamido)pyridine

Temperature

20 °C

A solution of pivaloyl chloride (13.4 g, 111 mmol) in DCM (20 mL) was slowly added to a cooled (0° C.) solution of pyridin-4-amine (10 g, 106 mmol) and triethylamine (26.7 g, 265 mmol) in DCM (80 mL). After addition, the icebath was removed and the resulting mixture was stirred at 20° C. for 6 hours. The mixture was poured into water (100 mL) and extracted with DCM (3×100 mL). The combined organic extract was washed with saturated NaHCO3 solution (100 mL) and brine (100 mL), dried over MgSO4, and concentrated under reduced pressure. The residue was re-crystallized from EtOAc/petroleum ether to give the desired product as white crystals (7.9 g, 40% yield). LCMS (ESI) m/z: 179.1 [M+H+].

1. additionAfter addition
2. customthe icebath was removed
3. additionThe mixture was poured into water (100 mL)
4. extractionextracted with DCM (3×100 mL)
5. extractionThe combined organic extract
6. washwas washed with saturated NaHCO3 solution (100 mL) and brine (100 mL)
7. dry with materialdried over MgSO4
8. concentrationconcentrated under reduced pressure
9. customThe residue was re-crystallized from EtOAc/petroleum ether

ORD record

ord-d03773d2a84f469c85d4d4040aeab4cb

Source dataset

uspto-grants-2014_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08697708B2