Diisopropylethylamine → HCID 118447873, compound

Participants

Reaction Steps

To a mixture of the product of Example 4, Step 2, 5-{7-[(3S)-3-methylpyrrolidin-3-yl]-2-(morpholin-4-yl)-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidin-4-yl}pyrimidin-2-amine hydrochloride (˜1.0 g, ˜1.77 mmol), 2-tert-butoxycarbonylamino-2-methyl-propionic acid (504 mg, 2.48 mmol) and DIEA (2.16 mL, 12.4 mmol) in 10 mL NMP, was added HATU (1.0 g, 2.67 mmol). The reaction was covered with foil and stirred at room temperature for 18 h. The reaction mixture was dropped into aqueous NaHCO3 and the resulting precipitate was collected by filtration. The filtrate was extracted with DCM (3 times). The filtrate and solids were combined, washed with brine, dried over MgSO4 and concentrated. The residue was purified by Biotage (40-FM cartridge) using a gradient of 0-10% MeOH/EtOAc as eluent to give the title compound (771 mg, 76%) as a foamy solid. 1H NMR (400 MHz, 80° C., DMSO-d6) δ 8.73 (s, 2 H), 6.71-6.54 (m, 3 H), 4.06-3.83 (m, 2 H), 3.70-3.41 (m, 12 H), 3.08 (t, J=8.1 Hz, 2 H), 2.47-2.35 (m, 1H, partially overlapped with DMSO), 2.10-2.01 (m, 1 H), 1.39-1.28 (m, 18 H). m/z (APCI+) for C28H41CN9O4568.3 (M+H)+.

Provenance & Evidence