4,5-Pyrimidinediamine, 6-chloro- → 6-Chloro-8-(2,6-dichloro-benzyl)-9H-purine

Participants

Reaction Conditions

Reaction Steps

To a mixture of 6-chloro-pyrimidine-4,5-diamine (100 mg, 0.694 mmol), (2,6-dichloro-phenyl)-acetaldehyde (260 mg, 1.38 mmol) and 1,4-dioxane (7 mL) was added 5% FeCl3.SiO2 (150 mg). The resulting mixture was heated to 100° C. in a sealed tube. After 24 h, the mixture was cooled to rt and filtered through a pad of diatomaceous earth, washing with EtOAc (3×10 mL). The filtrate was concentrated and the residue was purified by preparative reverse-phase HPLC to afford the title compound as a white solid (25 mg, 36%). MS (ESI): mass calcd. for C12H7Cl3N4, 311.9; m/z found, 313.0 [M+H]+. 1H NMR (CDCl3): 8.65 (s, 1H), 7.46 (d, J=8.1 Hz, 2H), 7.34-7.29 (m, 1H), 4.78 (s, 2H).

Provenance & Evidence