Methyl iodide → HCID 61360573, compound

Temperature

-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 record

ord-5b347886bd454004b47eaace57d7e4bc

Source dataset

uspto-grants-2015_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09115139B2