Reaktion #79889

Reaktionsgleichung

5-[4-(benzyloxy)phenyl]-4-chloro-7-(1,4-dioxaspiro[4.5]dec-8-yl)-7H-pyrrolo[2,3-d]pyrimidine

ammonium hydroxide

Ethyl acetate

sodium chloride

→

5-[4-(benzyloxy)phenyl]-7-(1,4-dioxaspiro[4.5]dec-8-yl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine

Ausbeute 81.0%

Lösungsmittel

dioxane

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturto cool to room temperature
2. 2
   SonstigeThe layers were partitioned
3. 3
   Extraktionthe aqueous layer was extracted with ethyl acetate (700 mL)
4. 4
   Waschenwashed with water
5. 5
   Trocknendried over magnesium sulfate
6. 6
   Sonstigethe solvent removed under reduced pressure
7. 7
   SonstigeThe compound was purified by flash chromatography on silica using 5% methanol in dichloromethane

Vorschrift

A mixture of 5-[4-(benzyloxy)phenyl]-4-chloro-7-(1,4-dioxaspiro[4.5]dec-8-yl)-7H-pyrrolo[2,3-d]pyrimidine (1.925 g, 4.01 mmol) and concentrated ammonium hydroxide (50 ml) in dioxane (50 mL) was heated at 120° C. in a pressure vessel for 20 hours. The reaction mixture was allowed to cool to room temperature. Ethyl acetate (300 mL) and saturated sodium chloride aqueous solution (300 mL) were added. The layers were partitioned and the aqueous layer was extracted with ethyl acetate (700 mL). The organic layers were combined, washed with water, dried over magnesium sulfate, and the solvent removed under reduced pressure. The compound was purified by flash chromatography on silica using 5% methanol in dichloromethane to give 1.457 g (81%) of 5-[4-(benzyloxy)phenyl]-7-(1,4-dioxaspiro[4.5]dec-8-yl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine. 1H NMR (DMSO-d6, 400 MHz) δ 8.13(s, 1H), 7.49-7.31(m, 8H), 7.121-7.100(d, 2H, J=8 Hz), 6.02(br s, 2H), 5.149(s, 2H), 4.681-4.620 (m, 1H), 3.94-3.88(m, 4H), 2.12-2.03(m, 2H), 1.93-1.90(m, 2H), 1.82-1.71(m, 4H); Waters 2690 Alliance HPLC (Symmetry Shield RP18 3.5 μm, 2.1×50 mm; 5%-95% acetonitrile-0.1 M ammonium acetate over 15 min, 0.5 mL/min) Rt 6.924 min.

Quelle