Reaktion #164462

Reaktionsgleichung

110

N-(6-chloro-9-((4R,5R,7R,8R)-8-hydroxy-7-(hydroxymethyl)-1,6-dioxaspiro[3.4]octan-5-yl)-9H-purin-2-yl)benzamide

cyclopropylamine

MeOH

NaOMe

→

6-cyclopropylamino-nucleoside

Ausbeute 76.0%

(4R,5R,7R,8R)-5-(2-amino-6-(cyclopropylamino)-9H-purin-9-yl)-7-(hydroxymethyl)-1,6-dioxaspiro[3.4]octan-8-ol

Ausbeute 76.0%

Reaktionsbedingungen

Aufarbeitung

1. 1
   EinengenThe mixture was concentrated in vacuo
2. 2
   Sonstigethe residue was purified by silica gel column chromatography (0 to 20% MeOH in CH2Cl2)

Vorschrift

110 (800 mg, 1.85 mmol) in cyclopropylamine (10 mL) was stirred at room temperature for 24 h. To the solution were added MeOH (10 mL) and 5.4 M NaOMe (1.71 mL, 9.26 mmol) and the resulting mixture was stirred at room temperature for 15 h. The mixture was concentrated in vacuo, and the residue was purified by silica gel column chromatography (0 to 20% MeOH in CH2Cl2) to give 6-cyclopropylamino-nucleoside 111 (500 mg, 76%) as a white solid. 1H NMR (400 MHz, CD3OD) δ: 8.02 (s, 1H), 6.21 (s, 1H), 4.53 (m, 2H), 4.43 (d, 1H, J=8.8 Hz), 3.96 (m, 1H), 3.82-3.77 (m, 2H), 2.91 (m, 1H), 2.56 (m, 1H), 2.27 (m, 1H), 0.83 (m, 2H), 0.60 (m, 2H). LCMS (ESI): 349 (M+H)+.

Quelle