Potassium Carbonate → N-(5-cyclopropyl-1H-pyrazol-3-yl)-5-ethynyl-2-(piperidin-1-yl)pyrimidin-4-amine
Reaktionsgleichung
[CH:1]1([C:4]2[NH:8][N:7]=[C:6]([NH:9][C:10]3[C:15]([C:16]#[C:17][Si](C)(C)C)=[CH:14][N:13]=[C:12]([N:22]4[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]4)[N:11]=3)[CH:5]=2)[CH2:3][CH2:2]1.C([O-])([O-])=O.[K+].[K+]>CCO>[CH:1]1([C:4]2[NH:8][N:7]=[C:6]([NH:9][C:10]3[C:15]([C:16]#[CH:17])=[CH:14][N:13]=[C:12]([N:22]4[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27]4)[N:11]=3)[CH:5]=2)[CH2:3][CH2:2]1Komponenten
4
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
A mixture of N-(5-cyclopropyl-1H-pyrazol-3-yl)-2-(piperidin-1-yl)-5-((trimethylsilyl)ethynyl)pyrimidin-4-amine (101 mg, 0.27 mmol), K2CO3 (74.5 mg, 0.54 mmol, 2.0 eq) in EtOH (4 ml) was stirred at room temperature for 1 h. The mixture was filtered, the filtration was washed with water, extracted with EtOAc, dried (Na2SO4). EtOAc was removed by evaporation, the residue was recrystalized from ether to afford compound N-(5-cyclopropyl-1H-pyrazol-3-yl)-5-ethynyl-2-(piperidin-1-yl)pyrimidin-4-amine (Compound 172) (68 mg, 81.9%). MS (m/z): 309.1 [M+H]+. 1H NMR (400 MHz, DMSO-d6): δ 0.66-0.68 (m, 2H), 0.95 (d, J=6.8 Hz, 2H), 1.53 (d, J=3.6 Hz, 4H), 1.63-1.66 (m, 2H), 1.89-1.93 (m, 1H), 3.75 (t, J=5.4 Hz, 4H), 4.54 (s, 1H), 6.25 (bs, 1H), 7.94 (bs, 1H), 8.14 (s, 1H), 12.17 (bs, 1H).