Reaktion #42071

Reaktionsgleichung

4-Methyl-3-[4-(5-pyrimidinyl)pyrimidin-2-ylamino]aniline

N,N-diisopropyl-N-ethylamine

1H-benzotriazol-1-yloxytripyrrolidinophosphonium hexafluorophosphate

4-[(S)-3-(t-butoxycarbonylamino)-2-oxopyrrolidin-1-ylmethyl]-3-trifluoromethylbenzoic acid

→

objective compound

4-[(S)-3-(t-butoxycarbonylamino)-2-oxopyrrolidin-1-ylmethyl]-3-trifluoromethyl-N-{4-methyl-3-[4-(5-pyrimidinyl)pyrimidin-2-ylamino]phenyl}benzamide

Lösungsmittel

water

N,N-dimethylformamide

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGthe mixture was stirred at room temperature for 18 hours
2. 2
   Extraktionfollowed by extraction with ethyl acetate
3. 3
   WaschenThe organic layer was washed in turn with an aqueous saturated sodium hydrogen carbonate solution and water
4. 4
   Trocknendried over anhydrous magnesium sulfate
5. 5
   workup.DISTILLATIONThe solvent was distilled off under reduced pressure
6. 6
   Sonstigethe residue was purified by silica gel column chromatography

Vorschrift

Eight hundred mg of 4-[(S)-3-(t-butoxycarbonylamino)-2-oxopyrrolidin-1-ylmethyl]-3-trifluoromethylbenzoic acid (Reference Example 17) was dissolved in 7 ml of anhydrous N,N-dimethylformamide, and 0.67 ml of N,N-diisopropyl-N-ethylamine and 1.00 g of 1H-benzotriazol-1-yloxytripyrrolidinophosphonium hexafluorophosphate (PyBOP) were added in turn, followed by stirring at room temperature for 30 minutes. 4-Methyl-3-[4-(5-pyrimidinyl)pyrimidin-2-ylamino]aniline (Reference Example 18) was added and the mixture was stirred at room temperature for 18 hours. The reaction solution was diluted with water, followed by extraction with ethyl acetate. The organic layer was washed in turn with an aqueous saturated sodium hydrogen carbonate solution and water, and then dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure and the residue was purified by silica gel column chromatography to obtain 453 mg of the objective compound as a pale yellow amorphous.

Quelle