Reaktion #169458

Reaktionsgleichung

7-[1-(Tetrahydro-pyran-2-yloxymethyl)-cyclopropyl]-7H-pyrrolo[2,3-d]pyrimidine

N-iodosuccinimide

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title compound

Ausbeute 79.0%

5-Iodo-7-[1-(tetrahydro-pyran-2-yloxymethyl)-cyclopropyl]-7H-pyrrolo[2,3-d]pyrimidine

Ausbeute 79.0%

Lösungsmittel

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe reaction mixture was quenched with water (8 mL)
2. 2
   Extraktionextracted with ethyl acetate (3×20 mL)
3. 3
   WaschenThe combined organic layer was washed with water (5×15 mL), brine (10 mL)
4. 4
   Trocknendried over sodium sulphate
5. 5
   Sonstigeevaporated in vacuo
6. 6
   SonstigeThe crude material was purified by column chromatography on silica gel (gradient of dichloromethane:methanol 100:0 to 99:1)

Vorschrift

To a stirred solution of 7-[1-(Tetrahydro-pyran-2-yloxymethyl)-cyclopropyl]-7H-pyrrolo[2,3-d]pyrimidine (Preparation 248, 390 mg, 1.43 mmol) in DMF (8 mL) was added N-iodosuccinimide (481.5 mg, 2.14 mmol) and stirred at room temperature for 4 hours. The reaction mixture was quenched with water (8 mL) and extracted with ethyl acetate (3×20 mL). The combined organic layer was washed with water (5×15 mL), brine (10 mL), dried over sodium sulphate and evaporated in vacuo. The crude material was purified by column chromatography on silica gel (gradient of dichloromethane:methanol 100:0 to 99:1) to afford the title compound as a solid in 79% yield, 450 mg.

Quelle