Triethylamine → HCID 89400369, compound

Temperature

55 °C

A solution of (S)-1-(5-fluoropyridin-2-yl)ethanamine (prepared as described in WO2006/123113, 235 mg, 1.68 mmol) in tetrahydrofuran (2 mL) was added to a stirred solution of 2,4-dichloropyrimidine (250 mg, 1.68 mmol) in tetrahydrofuran (2 mL) at ambient temperature. A solution of triethylamine (0.23 mL, 1.68 mmol) in tetrahydrofuran (2 mL) was then added dropwise and the reaction mixture was heated overnight at 55° C. After cooling to ambient temperature, the reaction mixture was diluted with water and extracted twice with ethyl acetate. The combined organic layers were washed with water and brine, dried over magnesium sulfate, filtered and the solvents were evaporated under reduced pressure. The residue was purified by reverse phase chromatography (C-18 silica from Waters©, water/acetonitrile/methanol as eluents [0.1% v/v formic acid buffered] 0% to 100%) to give the title compound (43 mg, 10%) as an oil.

1. temperatureAfter cooling to ambient temperature
2. extractionextracted twice with ethyl acetate
3. washThe combined organic layers were washed with water and brine
4. dry with materialdried over magnesium sulfate
5. filtrationfiltered
6. customthe solvents were evaporated under reduced pressure
7. customThe residue was purified by reverse phase chromatography (C-18 silica from Waters©, water/acetonitrile/methanol as eluents [0.1% v/v formic acid

ORD record

ord-818a4a6c8f3e4d4c877e1adff4167a31

Source dataset

uspto-grants-2015_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09034311B2