Sodium Carbonate → HCID 58938578, compound

Participants

Reaction Conditions

Reaction Steps

A suspension of 2-(dipropylamino)-5-iodo-3,7-dimethyl-3,7-dihydro-4H-pyrrolo[2,3-d]pyrimidin-4-one (115 mg, 0.296 mmol), 4-chloro-2-methylphenylboronic acid (76 mg, 0.446 mmol), sodium carbonate (47 mg, 0.443 mmol) and tetrakis(triphenylphosphine)palladium (34 mg, 0.0294 mmol) in 1,2-dimethoxyethane (1.5 ml), ethanol (0.75 ml) and water (0.75 ml) was stirred at 80° C. for 4 hours. After cooling, the reaction mixture was diluted with water and ethyl acetate. The insoluble material was removed off by filtration. The filtrate was extracted with ethyl acetate (×2). The combined organic layer was washed with brine (×1), dried over sodium sulfate and concentrated in vacuo. The residue was purified by silica gel column chromatography eluting with a 10-18% hexane/ethyl acetate gradient mixture. The fractions containing the title compound were purified again by column chromatography eluting with 18% hexane/ethyl acetate using silica gel coated with amine. The desired fractions were concentrated in vacuo, and the resulting oil was crystallized from hexane and washed with pentane to give 12 mg (11%) of the title compound.

Provenance & Evidence