Nitrogen → 5-isopropyl-N-methylpyridin-2-amine

Temperature

0 °C

A solution of 5-isopropyl-pyridin-2-ylamine (0.5 g, 3.67 mmol) in dry THF was purged with N2 and cooled to −78° C. n-BuLi (1.62 mL, 4.04 mmol) was added dropwise. The reaction was stirred at 0° C. for 0.5 h, and then iodomethane (0.25 mL, 4.04 mmol) was added dropwise. The resulting mixture was stirred overnight while warming to r.t. Water (20 mL) was added, and the mixture was extracted with EtOAc. The organic layer was dried over Na2SO4, concentrated, and purified by silica gel chromatography (10% to 30% EtOAc in PE) to give 200 mg (36%) of the title compound as a brown oil. [M+H] Calc'd for C9H14N2, 151. Found, 151.

1. additionwas added dropwise
2. stirringThe resulting mixture was stirred overnight
3. temperaturewhile warming to r.t
4. extractionthe mixture was extracted with EtOAc
5. dry with materialThe organic layer was dried over Na2SO4
6. concentrationconcentrated
7. custompurified by silica gel chromatography (10% to 30% EtOAc in PE)

ORD record

ord-7b88ec5d0e78410095cff08470740bd3

Source dataset

uspto-grants-2016_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09242968B2