Water → 2-(Cyclopropylmethyl)amino-5-ethynyl pyridine

To a 0° C. solution of 855 mg (3.50 mmol) of cyclopropylmethyl-(5-trimethylsilanylethynyl-pyridin-2-yl)-amine in 7 mL of THF, was slowly added 7.0 mL (7.0 mmol) of 1M TBAF in THF. The mixture was stirred for 2 h, then poured into water and extracted with Et2O. The Et2O was washed with brine. The washes were extracted once with Et2O, and the combined extracts were diluted with 10 mL of CH2Cl2 and left to sit for 10 min. The solution was then decanted from the water that had separated, and was dried with Na2SO4, filtered, concentrated, and chromatographed (1-20% EtOAc in hexanes) to provide 467 mg of 2-(cyclopropylmethyl)amino-5-ethynyl pyridine.

1. customTo a 0° C.
2. extractionextracted with Et2O
3. washThe Et2O was washed with brine
4. extractionThe washes were extracted once with Et2O
5. additionthe combined extracts were diluted with 10 mL of CH2Cl2
6. waitleft
7. waitto sit for 10 min
8. customThe solution was then decanted from the water that
9. customhad separated
10. dry with materialwas dried with Na2SO4
11. filtrationfiltered
12. concentrationconcentrated
13. customchromatographed (1-20% EtOAc in hexanes)

ORD record

ord-9022afb00f744d4286d92b47b7943632

Source dataset

uspto-grants-2009_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07514458B2