Methyl iodide → HCID 61360573, Verbindung

Temperatur

-78 °C

To a solution of 6-chloro-N-(cyclopropylmethyl)pyrazin-2-amine (0.60 g) in tetrahydrofuran (5 mL) was added dropwise n-butyllithium (3.06 mL, 1.6 M hexane solution) at −78° C. The mixture was stirred at −78° C. for 5 min, and iodomethane (1.02 mL) was added dropwise thereto. The mixture was stirred at −78° C. for 30 min, and further stirred at 0° C. for 1 hr. Saturated aqueous sodium thiosulfate solution (10 mL) was added, and the mixture was extracted with ethyl acetate. The aqueous layer was extracted again with ethyl acetate. The combined organic layer was washed with water and saturated brine, dried over magnesium sulfate, and concentrated. The residue was purified by silica gel column chromatography (solvent gradient: 5→15% ethyl acetate/hexane) to give the title compound (0.46 g, 70%) as a pale-yellow oil.

1. stirringThe mixture was stirred at −78° C. for 30 min
2. stirringfurther stirred at 0° C. for 1 hr
3. extractionthe mixture was extracted with ethyl acetate
4. extractionThe aqueous layer was extracted again with ethyl acetate
5. washThe combined organic layer was washed with water and saturated brine
6. dry with materialdried over magnesium sulfate
7. concentrationconcentrated
8. customThe residue was purified by silica gel column chromatography (solvent gradient: 5→15% ethyl acetate/hexane)

ORD-Eintrag

ord-016bc03cf2b14c829ad7bd49b43d4b87

Quelldatensatz

uspto-grants-2012_11

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08318722B2