Phthalimide → (S)-2-(2-(3-bromopyrazolo[1,5-a]pyrimidin-5-ylamino)-3-methylbutyl)isoindoline-1,3-dione

Participants

Reaction Steps

To a solution of isoindoline-1,3-dione (4.9 g, 34 mmol) in THF cooled to 0° C. was added triphenylphosphine (8.8 g, 34 mmol) and (S)-2-(3-bromopyrazolo[1,5-a]pyrimidin-5-ylamino)-3-methylbutan-1-ol (Example 15, Step 1; 6.7 g, 22 mmol) and the reaction stirred at ambient temperature until all reactants were dissolved. To the reaction was added (E)-diisopropyl diazene-1,2-dicarboxylate (8.2 g, 40 mmol) and the reaction was stirred for 2 hours at ambient temperature. The reaction was concentrated in vacuo and the material chromatographed using 20% EtOAc/dichloromethane as eluent to yield (S)-2-(2-(3-bromopyrazolo[1,5-a]pyrimidin-5-ylamino)-3-methylbutyl)isoindoline-1,3-dione (3.8 g, 40%).

Provenance & Evidence