Water → 3-(4-amino-1-((1-phenyl-1H-benzo[d]imidazol-2-yl)methyl)-1H-pyrazolo[3,4-d]pyrimidin-3-yl)prop-2-yn-1-ol

Participants

Reaction Steps

A mixture of 3-iodo-1-((1-phenyl-1H-benzo[d]imidazol-2-yl)methyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine 141 (1.5 g, 3.2 mmol), prop-2-yn-1-ol (0.4 g, 6.4 mmol), CuI (0.2 g, 0.64 mmol) and Pd(PPh3)2Cl2 (0.25 g, 0.32 mmol) in Et2NH (30 mL) was stirred at 25 for 2 hrs. Then the mixture was added H2O (50 mL) and extracted with CH2Cl2 (30 mL×3). The combined organic layers were concentrated in vacuo. The residue was treated with CH2Cl2 and filtered to give 152 (400 mg, yield 32%) as a yellow solid. LCMS (ESI), M+H+=394.15. 1HNMR (400 MHz, DMSO) δ 4.322-4.337 (d, J=6 Hz, 2H), 5.395-5.425 (t, J=6 Hz, 1H), 5.710 (s, 2H), 5.735 (s, 2H), 7.090-7.107 (d, J=6.8 Hz, 1H), 7.223-7.249 (m, 2H), 7.414-7.491 (s, 5H), 7.643-7.663 (d, J=8 Hz, 1H), 8.092 (s, 1H)

Provenance & Evidence