6-Methoxy-5-(1-methyl-1H-pyrazol-4-yl)pyridin-2-ylamine → N-(6-Methoxy-5-(1-methyl-1H-pyrazol-4-yl)pyridin-2-yl)-4,6-dimethyl-2-(4-methylthiazol-2-yl)-2,3,4,5-tetrahydropyrido[3,2-f][1,4]oxazepin-8-amine

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8-chloro-4,6-dimethyl-2-(4-methylthiazol-2-yl)-2,3,4,5-tetrahydropyrido[3,2-f][1,4]oxazepine (185 mg, 0.60 mmol), 6-methoxy-5-(1-methyl-1H-pyrazol-4-yl)pyridin-2-amine (122 mg, 0.60 mmol), Pd2dba3 (13.67 mg, 0.01 mmol), BINAP (18.59 mg, 0.03 mmol) and SODIUM TERT-BUTOXIDE (92 mg, 0.96 mmol) were weighed into a microwave vial. toluene (5 mL) was added and the vial was capped and flushed with argon. The mixture was heated to 100°C in a microwave apparatus for 2 h. The reaction mixture was diluted with dichloromethane and filtered. The solvents were evaporated and the residue was purified by column chromatography on Silica using a gradient of increasing concentration of methanol, from 0 to 8 %, in dichloromethane to give 163 mg og the title product . The enantiomers were separated by HPLC using a chiral stationary phase to give enantiomer 1 of N-(6-methoxy-5-(1-methyl-1H-pyrazol-4-yl)pyridin-2-yl)-4,6-dimethyl-2-(4-methylthiazol-2-yl)-2,3,4,5-tetrahydropyrido[3,2-f][1,4]oxazepin-8-amine (66.3 mg, 23.25 %) and enantiomer 2 of N-(6-methoxy-5-(1-methyl-1H-pyrazol-4-yl)pyridin-2-yl)-4,6-dimethyl-2-(4-methylthiazol-2-yl)-2,3,4,5-tetrahydropyrido[3,2-f][1,4]oxazepin-8-amine (65.2 mg, 22.86 %).

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