Tetrahydrofuran → Diisopropylethylamine
Reaktionsgleichung
Cl.Cl.[CH:3]1([C:6]2[N:11]=[CH:10][C:9](OC3C=CC(CCN)=CC=3)=CN=2)CC1.[CH2:22]1[CH2:26]OC[CH2:23]1.[CH3:27]N1C(=O)CCC1>>[CH3:9][CH2:10][N:11]([CH:22]([CH3:26])[CH3:23])[CH:6]([CH3:3])[CH3:27]Komponenten
4
Versuchsvorschrift
Crude {4-[(2-cyclopropylpyrimidin-5-yl)oxy]benzyl}methylamine dihydrochloride (0.115 g, 0.35 mmol) was dissolved in NMP (2.0 mL), THF (2.0 mL) and DIPEA (0.30 mL, 1.8 mmol) to form a yellow solution. (4S)-(4-Cyclopropyl-2,5-dioxoimidazolidin-4-yl)methanesulfonyl chloride (WO 2006/065215; 0.070 g, 0.28 mmol) was added portionwise during 5 minutes and the reaction mixture was stirred for 1 hour. The solvent was removed by evaporation and the residue was diluted with water and extracted twice with EtOAc. The combined organic phases were washed with water and concentrated. The crude product was purified by HPLC, using a 35 minutes gradient of 20% to 90% MeCN in water to give 0.081 g (61% yield) of the title compound as a colourless powder.