Sodium Carbonate → HCID 44203864, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 3-iodo-1-isopropyl-1H-pyrazolo[3,4-d]pyrimidin-4-amine (104) (1.88 g, 6.2 mmol), N-(6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[d]thiazol-2-yl)acetamide (I-5) (2.0 g, 6.3 mmol), Pd(OAc)2 (0.28 g, 1.24 mmol), triphenyl phosphine (0.98 g, 3.7 mmol) and Na2CO3 (3.3 g, 31 mmol) was dissolved in a mixture of DMF (5 mL), EtOH (2 mL) and H2O (2 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 chromatography eluting with DCM/MeOH (20/1) on a silica gel column (200-300 mesh) to afford the desired product N-(6-(4-amino-1-isopropyl-1H-pyrazolo[3,4-d]pyrimidin-3-yl)benzo[d]thiazol-2-yl)acetamide (501) (1.1 g, 48.2%) as a white solid. ESI-MS (M+H)+ m/z: 368.4.

Provenance & Evidence