Benzophenone imine → HCID 57494447, compound

Participants

Reaction Conditions

Reaction Steps

A dry flask was charged with 5-bromo-2-(1-propyl-pyrrolidin-3-yl)-pyrimidine (300 mg, 1.11 mmol), Pd2(dba)3 (tris(dibenzylideneacetonate) dipalladium (30 mg, 0.032 mmol)), rac-BINAP (2,2′-bis(diphenylphosphino)-1,1′-binaphthyl) (35 mg, 0.056 mmol), tBuONa (150 mg, 1.56 mmol), benzophenone imine (300 mg, 1.65 mmol) and toluene (4 ml). It was then evacuated, flushed with nitrogen and the mixture heated at 80° C. under microwave irradiations for 3 h. After filtration through a pad of celite, the solvent was removed under reduced pressure. The crude material was then dissolved in THF (10 ml) and 1 N aqueous HCl (3 ml) was added. The solution was stirred at room temperature for 45 min and the organic solvent was next removed under vacuo. The resulting aqueous phase was adjusted to pH˜9 with 2 N NaOH solution, washed with heptane:ethyl acetate, 2:1 (50 ml) and concentrated to give the crude amine.

Provenance & Evidence