HCID 71735444, compound → HCID 178439598, compound

Participants

Reaction Steps

Palladium (10 wt. % on activated carbon, 3.53 mg, 3.32 μmol) was added to a mixture of 3,3-dimethyl-1-(−3-((5-(prop-1-en-2-yl)pyrimidin-2-yl)amino)cyclobutyl)-1H-pyrrolo[2,3-b]pyridin-2(3H)-one (example 80, 58 mg, 0.166 mmol) in ethanol (1 mL) and ethyl acetate (0.5 mL) under an argon atmosphere. The reaction mixture was placed under a hydrogen atmosphere (balloon) and stirred at room temperature for 6 hours. The reaction mixture was filtered through celite, and the filtrate was concentrated to yield 1-(trans-3-((5-isopropylpyrimidin-2-yl)amino)cyclobutyl)-3,3-dimethyl-1H-pyrrolo[2,3-b]pyridin-2(3H)-one as a yellow solid. M+1: 352.3. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.19 (d, J=6.85 Hz, 6 H) 1.31 (s, 6 H) 2.23-2.39 (m, 2 H) 2.76 (spt, J=6.94 Hz, 1 H) 3.14-3.26 (m, 2 H) 4.47-4.59 (m, 1 H) 5.16 (quin, J=8.51 Hz, 1 H) 7.08 (dd, J=7.24, 5.28 Hz, 1 H) 7.53 (br. d, J=6.50 Hz, 1 H) 7.76 (dd, J=7.24, 1.57 Hz, 1 H) 8.21 (dd, J=5.28, 1.56 Hz, 1 H) 8.24 (s, 2 H)

Provenance & Evidence