Benzylamine → HCID 67130069, compound

Participants

Reaction Conditions

Reaction Steps

To a vial was added 2-chloro-N-(5-cyclopropyl-1H-pyrazol-3-yl)furo[3,2-d]pyrimidin-4-amine (0.20 g, 0.73 mmol), benzyl amine (0.79 mL, 7.3 mmol), X-Phos (0.02 g, 0.04 mmol) K2CO3 (0.50 g, 3.6 mmol), and Pd2dba3 (0.04 g, 0.04 mmol). To the vial was added t-BuOH (3.6 mL) and tube was sealed. The tube was evacuated, purged with nitrogen three times and stirred over night at about 100° C. To the mixture was added additional benzyl amine (0.79 mL, 7.3 mmol), X-Phos (0.02 g, 0.04 mmol), and Pd2dba3 (0.04 g, 0.04 mmol). The mixture was stirred at about 100° C. for about 26 h. The mixture was filtered, the filter pad was washed with DCM and then the solvent was removed in vacuo. The crude material was added to a silica gel column and was eluted with EtOAc/DCM (50% to 100% gradient) followed by 2.0 M NH3 in EtOH/DCM (2%) to give N2-benzyl-N4-(5-cyclopropyl-1H-pyrazol-3-yl)furo[3,2-d]pyrimidine-2,4-diamine (0.013 g, 5%). LC/MS Rt=1.30 min; MS m/z 347.29 (M+H)+. Syk IC50=B.

Provenance & Evidence