(S)-N4-(1-(5-Fluoropyridin-2-yl)ethyl)-N2-(2-methoxypyridin-3-yl)pyrimidine-2,4-diamine → (S)-3-(4-(1-(5-fluoropyridin-2-yl)ethylamino)pyrimidin-2-ylamino)pyridin-2(1H)-one

Participants

Reaction Conditions

Reaction Steps

A suspension of (S)—N4-(1-(5-fluoropyridin-2-yl)ethyl)-N2-(2-methoxypyridin-3-yl) pyrimidine-2,4-diamine (Preparation 1 b, 11 mg, 0.03 mmol) in 48% aqueous hydrogen bromide solution (2 mL) was stirred and heated to 100° C. for 5 hours. After cooling to ambient temperature, the reaction mixture was diluted with water and extracted with dichloromethane. The pH of the aqueous phase was then adjusted to ca. 8 with 2M aqueous sodium hydroxide solution and extracted (×3) with dichloromethane. The combined organic extracts were washed with water and brine, dried (MgSO4), filtered and the solvent evaporated under reduced pressure to yield the title compound (4 mg, 38%) as a solid.

Provenance & Evidence