Toluene → 4-Chloro-7-isopropyl-5-(4-methoxyphenyl)pyrrolo[2,3-d]pyrimidine

Participants

Reaction Conditions

Reaction Steps

A mixture of 4-chloro-5-iodo-7-isopropylpyrrolo[2,3-d]pyrimidine (2.8 g), 4-methoxybenzeneboronic acid (1.32 g), bis(triphenylphosphine)palladium (II) chloride (625 mg), toluene (85 ml), ethanol (11 ml), water (22 ml) and sodium bicarbonate (2.2 g) was heated under nitrogen at 105° C. for 18 hours. The mixture was allowed to cool to ambient temperature and then partitioned between ethyl acetate (100 ml) and brine (100 ml). The organic layer was separated and the aqueous layer was washed with ethyl acetate (2×50 ml). The combined organic layers were washed with water, dried, filtered and evaporated under reduced pressure to give a black oil which solidified on cooling. This material was purified by flash column chromatography on silica using cyclohexane/ethyl acetate (7:3) as the mobile phase. Appropriate fractions were combined and concentrated under reduced pressure to give a yellow oil which solidified on standing to give 4-chloro-7-isopropyl-5-(4-methoxyphenyl)pyrrolo[2,3-d]pyrimidine. The structure was confirmed by 1H nmr.

Provenance & Evidence