Sodium Carbonate → 1-isopropyl-3-(2-(methylamino)benzo[d]thiazol-6-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine

Participants

Reaction Conditions

Reaction Steps

A mixture of 3-iodo-1-isopropyl-1H-pyrazolo[3,4-d]pyrimidin-4-amine (104) (47 mg, 0.16 mmol), N-methyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[d]thiazol-2-amine (703 (37 mg, 0.13 mmol), Pd(OAc)2 (6 mg, 0.027 mmol), triphenyl phosphine (20 mg, 0.076 mmol) and Na2CO3 (69 mg, 0.65 mmol) was dissolved in a mixture of DMF (4 mL), EtOH (4 mL) and H2O (2 mL). The resulting mixture was degassed and back-filled with argon three times and then stirred at 90° C. for 1.5 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 chromatography on silica gel (200-300 mesh) eluting with DCM/MeOH (20/1) to give the desired product 1-isopropyl-3-(2-(methylamino)benzo[d]thiazol-6-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine (704) (15 mg, 34.1%) as a pale solid. ESI-MS (M+H)+ m/z: 340.05.

Provenance & Evidence