2-Amino-5-methylpyridine → HCID 90041616, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of 5-methylpyridin-2-amine (72.1 mg, 666 μmol), 2-bromo-N-(1-hydroxy-2-methylpropan-2-yl)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (197 mg, 444 μmol), (R)-(+)-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (13.8 mg, 22.2 μmol), palladium(II) acetate (24.9 mg, 111 μmol) and sodium tert-butoxide (107 mg, 1.11 mmol) was added DMF (2 mL) and toluene (1 mL) then heated in a microwave at 140° C. for 20 min. The dark mixture generated was poured into water and extracted with ethyl acetate (3×). The organic layers were combined, washed with brine (2×), dried over magnesium sulfate and purified by chromatography (silica, 65-100% ethyl acetate in hexanes) to give N-(1-hydroxy-2-methylpropan-2-yl)-2-(5-methylpyridin-2-ylamino)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (66 mg, 140 μmol, 32%) as a light yellow solid. MS (EI/CI) m/z: 471.4.

Provenance & Evidence