Methyl iodide → 5-Bromo-N-methylpyridin-2-amine

NaH (47.3 mg, 1.971 mmol) and 5-bromo-2-pyridinamine (310 mg, 1.792 mmol, available from Aldrich) were added to N,N-Dimethylformamide (DMF) (7 mL) and stirred in an ice bath for 30 mins. The reaction mixture was then allowed to warm to room temperature and methyl iodide (0.123 mL, 1.971 mmol) was added and the reaction mixture stirred for 24 hr. The reaction mixture was partitioned between DCM (20 mL) and water (20 mL) and the organic layer washed with more water (20 mL) before being dried through an hydrophobic frit and concentrated. The residue was dissolved in DCM and purified by SP4 on a 25+S silica cartridge using a gradient of 10%-40% EtOAc in cyclohexane. Appropriate fractions were collected and concentrated to yield the desired product as a white solid (79.1 mg). LCMS (Method C): Rt 0.39, MH+=187

1. stirringthe reaction mixture stirred for 24 hr
2. customThe reaction mixture was partitioned between DCM (20 mL) and water (20 mL)
3. washthe organic layer washed with more water (20 mL)
4. custombefore being dried through an hydrophobic frit
5. concentrationconcentrated
6. dissolutionThe residue was dissolved in DCM
7. custompurified by SP4 on a 25+S silica cartridge
8. customAppropriate fractions were collected
9. concentrationconcentrated

ORD record

ord-62d4a30bb12f449587ab7aa55963bc3d

Source dataset

uspto-grants-2014_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08697725B2