Methylamine → 5-bromo-2-chloro-N-methylpyrimidin-4-amine

Temperature

-20 °C

5-Bromo-2,4-dichloro-pyrimidine (2.41 g, 10.6 mmol) is slowly treated with methylamine (8 M in EtOH, 3.3 mL) in THF (15 mL) at about −20° C. After stirring for 30 minutes at about −20° C., the reaction mixture is partitioned between CHCl3 and saturated NaHCO3. The aqueous layer is extracted with additional CHCl3 twice and the combined organic layer is dried over MgSO4, filtered and concentrated. The crude product is purified by column chromatography (SiO2, EtOAc/Hexane=3/7) to give 1.76 g (75%) of (5-bromo-2-chloro-pyrimidin-4-yl)-methylamine as a white solid.

1. customthe reaction mixture is partitioned between CHCl3 and saturated NaHCO3
2. extractionThe aqueous layer is extracted with additional CHCl3 twice
3. dry with materialthe combined organic layer is dried over MgSO4
4. filtrationfiltered
5. concentrationconcentrated
6. customThe crude product is purified by column chromatography (SiO2, EtOAc/Hexane=3/7)

ORD record

ord-5eb220b146864183bbccf999ad9efa93

Source dataset

uspto-grants-2010_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07642255B2