Methylamine → 2,5-dichloro-N-methylpyrimidin-4-amine

To a cooled (0° C.) solution of 2,4,5-trichloropyrimidine (2.0 g, 11 mmol) in methanol (30 mL) was added dropwise a 2 M solution of methylamine in methanol (6.3 mL). The reaction was allowed to warm to room temperature and stirred overnight. The reaction was then concentrated and redissolved in DCM. The solution was washed with sat. NaHCO3, brine, dried over Na2SO4, filtered and concentrated. The crude product was purified by column chromatography (0-40% EtOAc in heptane) to give 2,5-dichloro-N-methylpyrimidin-4-amine (0.9 g, 50%). 1H-NMR (DMSO): δ 8.13 (s, 1H), 7.89 (s, 1H), 2.86 (d, J=4.5, 3H).

1. concentrationThe reaction was then concentrated
2. dissolutionredissolved in DCM
3. washThe solution was washed with sat. NaHCO3, brine
4. dry with materialdried over Na2SO4
5. filtrationfiltered
6. concentrationconcentrated
7. customThe crude product was purified by column chromatography (0-40% EtOAc in heptane)

ORD record

ord-6fd66cec6e19453fa687d4a1844f4c3c

Source dataset

uspto-grants-2014_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08815882B2