Sodium Carbonate → (2S)-1-(4-(3-(6-amino-5-methylpyridin-3-yl)-1-isopropyl-1H-pyrazol-4-yl)pyrimidin-2-ylamino)propan-2-ol

Participants

Reaction Conditions

Reaction Steps

To a solution of (2S)-1-(4-(3-iodo-1-isopropyl-1H-pyrazol-4-yl)pyrimidin-2-ylamino)propan-2-ol (B-1-3) (0.52 g, 1.34 mmol) in toluene (21 mL) and EtOH (7 mL) were added 3-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amine (B-3-2) (1 g, 2.68 mmol in theory) and 2 N aq. Na2CO3 (2 mL). The resulting mixture was degassed under N2 for 2 minutes. Then Pd(PPh3)4 (0.15 g, 0.134 mmol) was added and the mixture was degassed again. The reaction was heated to 80-90° C. and stirred overnight. The mixture was cooled. The organic layer was separated and concentrated. The residue was purified by prep. HPLC to afford (2S)-1-(4-(3-(6-amino-5-methylpyridin-3-yl)-1-isopropyl-1H-pyrazol-4-yl)pyrimidin-2-ylamino)propan-2-ol (B-3) (0.057 g, 11.6%) as a light yellow solid.

Provenance & Evidence