2,4-Dichloropyrimidine → N2,N4-bis(6-Hydroxy-3-quinolinyl)-2,4-pyrimidinediamine

Participants

Reaction Steps

A mixture of 6-hydroxy-3-aminoquinoline di-hydrobromide (0.064 g, 0.2 mmol) and 2,4-dichloropyrimidine (0.148 g, 1 mmol) in IPA (1 mL) was heated at reflux overnight. The reaction was cooled to RT and a yellow solid was filtered off and washed with IPA. The solid was purified by flash chromatography in CH2Cl2/MeOH/NH4OH (90/10/1). The fractions containing the compound were combined and the solvents were removed under vacuum. The residue was purified by reverse-phase preparative HPLC (CH3CN/water/TFA) to give the bis-trifluoroacetate of the title compound as a yellow solid. MS (MH+)=397.2, Calc'd for: C22H16N6O2—396.4.

Provenance & Evidence