Sodium Carbonate → HCID 118436211, compound

Participants

Reaction Conditions

Reaction Steps

To a vial containing tert-butyl(3S)-3-{4-chloro-2-[(3S)-3-methylmorpholin-4-yl]-5,6-dihydro-7H-pyrrolo[2,3-d]pyrimidin-7-yl}-3-methylpyrrolidine-1-carboxylate hydrochloride (3796 mg, 8.68 mmol) in 1,4-dioxane (41.2 mL) was added 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidin-2-amine (2492 mg, 11.28 mmol), and 1 M aqueous Na2CO3 (26 mL). Nitrogen was bubbled through the suspension for a few minutes before PdCl2(dppf)-DCM (516 mg, 0.632 mmol) was added and the mixture was heated in a microwave reactor at 120° C. for 30 min. The mixture was filtered through a pad of Celite® rinsing with EtOAc, and the filtrate was concentrated. The residue was purified by ISCO (80 g cartridge) using a gradient of 25-100% EtOAc/heptanes to give the title compound (3.94 g, 91%) as a yellow foamy solid. 1H NMR (400 MHz, DMSO-d6) δ 8.73 (s, 2 H), 6.60 (s, 2 H), 4.64-4.54 (m, 1 H), 4.23 (dd, J=13.5, 2.3 Hz, 1 H), 3.89 (dd, J=11.2, 3.4 Hz, 1 H), 3.79-3.35 (m, 8 H), 3.33-3.24 (m, 1 H), 3.19-3.05 (m, 3 H), 2.44-2.30 (m, 1 H), 2.10-1.95 (m, 1 H), 1.42 (s, 9 H), 1.32 (s, 3 H), 1.21 (d, J=6.7 Hz, 3 H). m/z (APCI+) for C25H36N8O3 497.6 (M+H)+.

Provenance & Evidence