Tetrabutylammonium Fluoride → 2-(4-Ethynyl-1H-pyrazol-1-yl)-N,N-dimethylacetamide

N,N-Dimethyl-2-(4-((trimethylsilyl)ethynyl)-1H-pyrazol-1-yl)acetamide (Preparation 100, 0.55 g, 2.2 mmol) was dissolved in dry THF (10 ml). To the stirred solution was then added a solution of TBAF in THF (2.4 ml of a 1M solution in THF, 2.4 mmol). After 20 minutes the reaction was concentrated in vacuo and the residue taken up in ethyl acetate. The organic solution was washed with water, brine and dried over sodium sulphate. The organic solution was then concentrated in vacuum and the crude product purified by silica gel column chromatography eluting with neat ethyl acetate to afford the title compound as a pale brown powder (0.3 g, 77%). 1H-NMR (500 MHz, CDCl3): δ 2.98 (s, 3H), 3.01 (s, 1H), 3.07 (s, 3H), 4.95 (s, 2H), 7.62 (s, 1H), 7.69 (s, 1H).

1. concentrationAfter 20 minutes the reaction was concentrated in vacuo
2. washThe organic solution was washed with water, brine
3. dry with materialdried over sodium sulphate
4. concentrationThe organic solution was then concentrated in vacuum
5. customthe crude product purified by silica gel column chromatography
6. washeluting with neat ethyl acetate

ORD record

ord-637ffe4abf464c3389c79f5a0d92e1d5

Source dataset

uspto-grants-2016_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09371319B2