Potassium Carbonate → HCID 68754980, compound

Participants

Reaction Conditions

Reaction Steps

To a flask was added 2-chloro-N-cyclopropylfuro[3,2-d]pyrimidin-4-amine (10.5 g, 50.1 mmol, Example #3, Step C), tert-butyl 6-amino-1H-indazole-1-carboxylate (14.02 g, 60.1 mmol, Frontier), K2CO3 (8.31 g, 60.1 mmol) and t-BuOH (334 mL). The reaction vessel was purged under vacuum and vented with N2 three times. To the mixture was added Pd2dba3 (2.75 g, 3.01 mmol) and X-Phos (2.87 g, 6.01 mmol). The reaction vessel was purged under vacuum and vented with N2. The mixture was heated to about 85° C. for about 3 days. The mixture was diluted with EtOAc (1000 mL) and washed with water (1000 mL). The organic layer was dried with MgSO4, filtered through a pad of Celite® and concentrated in vacuo. The residue was purified by column chromatography (300 g silica gel, DCM/MeOH 1:0 to 10:1) to give a solid. The material was further purified by column chromatography (300 g silica gel, DCM/EtOAc 1:0 to 0:1) to give tert-butyl 6-(4-(cyclopropylamino)furo[3,2-d]pyrimidin-2-ylamino)-1H-indazole-1-carboxylate (9.78 g, 48%): LC/MS (Table 2, Method u) Rt=1.48 min; MS m/z: 407 (M+H)+

Provenance & Evidence