Water → ethyl 4-(3-(methylamino)phenyl)-7H-pyrrolo[2,3-d]pyrimidine-5-carboxylate

Participants

Reaction Conditions

Reaction Steps

To a nitrogen purged mixture of ethyl 4-chloro-7H-pyrrolo[2,3-d]pyrimidine-5-carboxylate (300 mg, 1.33 mmol) and N-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (465 mg, 1.99 mmol) in 2 M aqueous sodium carbonate solution (3.32 mL, 6.65 mmol) and dioxane (10 mL) was added SiliaCat® heterogeneous catalysts DPP-Pd (loading=0.28 mmol/g, 950 mg, 0.266 mmol). The reaction mixture was heated by microwave irradiation at 150° C. in a sealed microwave vessel for 30 minutes. Water (5 mL) was added to the reaction mixture and then the biphasic mixture was filtered. The organic layer was separated and the aqueous layer was extracted with ethyl acetate (×3). The combined organic layers were dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by chromatography on silica eluting with 0-100% ethyl acetatehexane to give ethyl 4-(3-(methylamino)phenyl)-7H-pyrrolo[2,3-d]pyrimidine-5-carboxylate. LRMS (ESI) calc'd for C16H17N4O2[M+H]+: 297, found 297.

Provenance & Evidence