Reaktion #2381107

Reaktionsgleichung

compound 50

(1S, 2R, 3S, 4R)-4-(6-Amino-2-Chloro-9H-Purin-9-yl) Cyclopentane-1,2,3-triol

phenylethylamine

→

compound 51

Ausbeute 70.0%

(1S, 2R, 3S, 4R)-4-(6-Amino-2-Phenylethylamino-9H-Purin-9-yl)Cyclopentane-1,2,3-triol

Ausbeute 70.0%

Lösungsmittel

EtOH

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe solvent was removed by rotary evaporation

Vorschrift

To a suspension of compound 50 (300 mg, 1.05 mmol) in absolute EtOH (10 mL) was added phenylethylamine (300 mg, 2.45 mmol). This mixture was heated at 90° C. for 3 days. The solvent was removed by rotary evaporation, and the residue was subjected to column chromatography on silica gel (CH2Cl2 -MeOH) to give compound 51 (272 mg, 70%) as a yellow solid: mp. 200° C. (dec.); 1H NMR (DMSO-d6) δ 1.77-1.90 (m, 1 H, H-5'), 2.50-2.60 (m, 1 H, H-5'), 2.8 (m, 4 H, 2 x CH2), 3.75 (m, 1 H, H-2'), 3.89 (m, 1 H, H-1'), 4.40-4.52 (m, 1 H, H-3'), 4.62-4.81 (m, 1 H, H-4'), 4.87 (d, 1 H, J=3.6 Hz, OH), 5.01 (d, 1 H, J=6.6 Hz, OH), 5.36 (d, 1 H, J=4.8 Hz, OH), 7.22 (s, 2 H, NH2), 7.48 (m, 5 H, Ph), 8.48 (s, 1 H, H-8).

Quelle