Sodium Hydroxide → 5-(1,1-Dimethoxy-ethyl)-pyrazin-2-ylamine

Temperature

25 °C

A solution of N-[5-(1,1-dimethoxy-ethyl)-pyrazin-2-yl]-2,2-dimethyl-propionamide (1.73 g, 6.47 mmol) in ethanol (13 mL) was treated with a 2N aqueous sodium hydroxide solution (11 mL, 22 mmol). The reaction was stirred at 25° C. for 63 h and then was heated at 65° C. for 1.5 h. The reaction mixture was then diluted with ethyl acetate (200 mL) and washed with a saturated aqueous sodium chloride solution (75 mL). The aqueous layer was back-extracted with ethyl acetate (100 mL). The combined organic layers were dried over magnesium sulfate, filtered, and concentrated in vacuo. Biotage chromatography (FLASH 40M, Silica, 4% methanol/methylene chloride) afforded impure 5-(1,1-dimethoxy-ethyl)-pyrazin-2-ylamine as a yellow solid. This material was re-purified via Biotage chromatography (FLASH 40L, Silica, 7/3 ethyl acetate/hexanes) to afford still impure 5-(1,1-dimethoxy-ethyl)-pyrazin-2-ylamine as a light yellow solid (880.4 mg, 74%) which used without further purification and characterization.

1. temperaturewas heated at 65° C. for 1.5 h
2. washwashed with a saturated aqueous sodium chloride solution (75 mL)
3. extractionThe aqueous layer was back-extracted with ethyl acetate (100 mL)
4. dry with materialThe combined organic layers were dried over magnesium sulfate
5. filtrationfiltered
6. concentrationconcentrated in vacuo

ORD record

ord-36f2e23fc1904523b9aea26a98e0d93c

Source dataset

uspto-grants-2006_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07132425B2