Diethylamine → tert-Butyl N-[(3S)-1-methyl-2-oxo-3-[3-[4-[4-(trifluoromethyl)phenyl]pyrimidin-2-yl]prop-2-ynyl]pyrrolidin-3-yl]carbamate

Participants

Reaction Conditions

Reaction Steps

Copper iodide (25.51 mg, 0.1300 mmol), followed by PdCl2(Ph3P)2 (47.01 mg, 0.0700 mmol) was added portionwise to a solution of 2-iodo-4-[4-(trifluoromethyl)phenyl]pyrimidine (which may be prepared as described in Description 6) (703.46 mg, 2.01 mmol), tert-butyl N-[(3S)-1-methyl-2-oxo-3-prop-2-ynyl-pyrrolidin-3-yl]carbamate (which may be prepared as described in D4) (338 mg, 1.34 mmol) and Et2NH (0.69 mL, 6.7 mmol) in THF (10 mL) under N2 and the reaction was stirred at 20° C. for 18 hrs. The reaction was diluted with EtOAc and water was added. The phases were separated and the organic layer was dried (Na2SO4) and the solvent evaporated to afford a brown oil. This was purified by using a Biotage SP4, with a 25 g SNAP cartridge, eluting with 0 to 100% EtOAc in i-hexane to afford tert-butyl N-[(3S)-1-methyl-2-oxo-3-[3-[4-[4-(trifluoromethyl)phenyl]pyrimidin-2-yl]prop-2-ynyl]pyrrolidin-3-yl]carbamate (D7) (555 mg, 1.17 mmol, 87.3% yield) as a yellow oil.

Provenance & Evidence