2,6-Diaminopyridine → N2-(6-chloropyrimidin-4-yl)pyridine-2,6-diamine

Participants

Reaction Conditions

Reaction Steps

A mixture of 2,6-diaminopyridine (1.530 g, 14.020 mmol) and 4,6-dichloropyrimidine (2.610 g, 17.519 mmol) in 15 mL of n-butanol in a sealed vial was heated at 100° C. for 72 h. The dark brown sample was cooled, was concentrated to remove most of the n-butanol, and was then partitioned between EtOAc and sat. NaHCO3 solution. An emulsion formed, the sample was filtered through a pad of Celite and the layers were separated. The organic extract was washed with sat. KH2PO4 and brine solutions, was dried (MgSO4), was filtered and was concentrated to brown oily-solid. The sample was suspended into 50 mL of CH2Cl2, was cooled and was filtered to give 1.017 g of N-(6-chloro-pyrimidin-4-yl)-pyridine-2,6-diamine as yellow-orange solid. MS (ES) (m/z) 222/224 (M+1, 100/63%). TLC (SiO2, 50% EtOAc in hexanes): Rf 0.33.

Provenance & Evidence