Sodium t-butoxide → HCID 178426487, compound

Participants

Reaction Conditions

Reaction Steps

To a glass microwave vial was added 2-(3-chloropyrazin-2-yl)-2-methyl-N-(trans-4-((5-methylpyridin-2-yl)amino)cyclohexyl)propanamide (0.2148 g, 0.554 mmol), RuPhos precatalyst (0.024 g, 0.033 mmol), and sodium tert-butoxide (0.106 g, 1.107 mmol) in dry dioxane (0.554 ml). The mixture was sealed and stirred at 80° C. for 3 hours. The mixture was allowed to cool to room temperature then the crude product was adsorbed onto a plug of silica gel and chromatographed through a Biotage SNAP HP-silica gel column (25 g), eluting with a gradient of 0% to 5% methanol in dichloromethane, to provide 7,7-dimethyl-5-(trans-4-((5-methylpyridin-2-yl)amino)cyclohexyl)-5H-pyrrolo[2,3-b]pyrazin-6(7H)-one (0.0178 g, 0.051 mmol, 9.15% yield). M+1: 324. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.38 (s, 6 H) 1.50-1.72 (m, 3 H) 2.18 (s, 3 H) 2.23-2.35 (m, 2 H) 3.37-3.48 (m, 2 H) 4.36-4.46 (m, 1 H) 4.71-4.77 (m, 1 H) 5.27 (quin, J=8.90 Hz, 1 H) 6.26 (d, J=8.00 Hz, 1 H) 6.92-6.99 (m, 1 H) 7.42 (d, J=5.87 Hz, 1 H) 7.90-7.97 (m, 1 H) 8.15-8.20 (m, 1 H)

Provenance & Evidence