Sodium Carbonate → HCID 44225402, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 3-iodo-1-isopropyl-1H-pyrazolo[3,4-d]pyrimidin-4-amine (601 (1.21 g, 3.68 mmol), N-(6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[d]thiazol-2-yl)acetamide (I-5) (1.18 g, 3.71 mmol), Pd(OAc)2 (0.17 g, 0.75 mmol), triphenyl phosphine (0.59 g, 2.22 mmol) and Na2CO3 (1.98 g, 18.6 mmol) was dissolved in a mixture of DMF (3 mL), EtOH (1.5 mL) and H2O (1.5 mL). The resulting mixture was degassed and back-filled with argon three times and then stirred at 80° C. for 4 h. The mixture was allowed to cool to room temperature and filtered. The filtrate was concentrated in vacuo. The crude product was purified by flash column chromatography on silica gel (200-300 mesh) eluting with DCM/MeOH (20/1) to give the desired product, N-(6-(4-amino-1-cyclopentyl-1H-pyrazolo[3,4-d]pyrimidin-3-yl)benzo[d]thiazol-2-yl)acetamide (602) (0.52 g, 35.9%) as an off-white solid. ESI-MS (M+H)+ m/z: 394.1.

Provenance & Evidence