6-[(1-Methyl-4-phenyl-1H-imidazol-5-yl)ethynyl]pyrimidine-4,5-diamine → 6-(1-Methyl-4-phenyl-1H-imidazol-5-yl)-5H-pyrrolo[3,2-d]pyrimidin-4-amine

Participants

Reaction Steps

6-[(1-Methyl-4-phenyl-1H-imidazol-5-yl)ethynyl]pyrimidine-4,5-diamine (intermediate 90) (50 mg) and CuI (3 mg) in DMF (2 mL) were heated at 110° C. under an inert atmosphere for 4 hours. The reaction mixture was loaded on to a 1 g SCX column prewashed with DCM:MeOH (3:1). The column was eluted with DCM:MeOH (3:1) and then the product eluted with 7N NH3/MeOH:DCM:MeOH (1:3:1). The product fraction was concentrated and then purified by flash chromatography on silica eluting with DCM:MeOH (9:1) to afford the title compound as a yellow solid (3 mg, 6%);

Provenance & Evidence