Reaktion #303937

Reaktionsgleichung

sodium hydride

(2-(2-methoxyphenyl)-8-methylquinolin-3-yl)methanol

6-Chloropurine

DABCO

purine DABCO

→

3-((9H-purin-6-yloxy)methyl)-2-(2-methoxyphenyl)-8-methylquinoline

Lösungsmittel

DMSO

DMSO

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigePrepared

Vorschrift

Prepared according to modified Procedure L. 6-Chloropurine (0.077 g, 0.5 mmol, 2 eq) and DABCO (0.112 g, 1 mmol, 4 eq) were stirred in DMSO (0.7 mL) at room temperature for 5 h. In a separate flask, sodium hydride (0.040 g, 1 mmol, 4 eq) was added portion-wise to a stirring solution of (2-(2-methoxyphenyl)-8-methylquinolin-3-yl)methanol (0.070 g, 0.25 mmol) in DMSO (0.5 mL), and after 30 minutes, the purine-DABCO salt was added to this mixture. The reaction stirred at room temperature 18 h. 3-((9H-purin-6-yloxy)methyl)-2-(2-methoxyphenyl)-8-methylquinoline [PI3Kδ IC50=38 nM] was isolated as a white solid after purification on a silica column. 1H NMR (400 MHz, DMSO-d6) δ ppm 13.41 (1H, s), 8.51 (1H, s), 8.39 (1H, s), 7.87 (1H, d, J=7.8 Hz), 7.65 (1H, d, J=7.0 Hz), 7.49-7.56 (1H, m), 7.34-7.46 (2H, m), 7.12 (1H, d, J=8.2 Hz), 7.03 (1H, t, J=7.2 Hz), 5.58 (2H, s), 3.72 (3H, s), 2.69 (3H, s) Mass Spectrum (ESI) m/e=398.2 (M+1)

Quelle