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ord-d9a19803873546349da1be049890a71d
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8-(2,5-dichloropyridin-4-ylamino)-2-methyl-3,4-dihydroisoquinolin-1(2H)-one (100 mg, 0.31 mmol), 1-methyl-1H-pyrazol-5-amine (60.3 mg, 0.62 mmol), sodium 2-methylpropan-2-olate (44.7 mg, 0.47 mmol), 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (38.7 mg, 0.06 mmol) and TRIS(DIBENZYLIDENEACETONE)DIPALLADIUM (28.4 mg, 0.03 mmol) were suspended in dioxane (2 mL) and sealed into a microwave tube. The reaction was degased, purged with nitrogen and heated to 150 °C over a period of 30 minutes in the microwave reactor. Reaction was filtered, washed with CH2Cl2 and concentrated to dryness. The reaction mixture was purified by preparative HPLC using a Waters X-Bridge reverse-phase column (5 microns silica, 30 mm diameter, 150 mm length) and decreasingly polar mixtures of water (containing 1% acetic acid) and acetonitrile as eluent. The fractions containing product were combined and basified with saturated aqueous solution of NaHCO3. Aqueous layer was extracted with CH2Cl2 (2x15 mL). Organic layer was washed with brine, dried over MgSO4 and concentrated to dryness to afford 8-(5-chloro-2-(1-methyl-1H-pyrazol-5-ylamino)pyridin-4-ylamino)-2-methyl-3,4-dihydroisoquinolin-1(2H)-one (57.0 mg, 48.0 %) as a yellow crystalline solid.