Reaktion #79808

Reaktionsgleichung

diethylazodicarboxylate

4-chloro-5-iodo-7H-pyrrolo[2,3-d]pyrimidine

2-methylperhydrocyclopenta[c]pyrrol-5-ol

triphenylphosphine

→

4-chloro-5-iodo-7-(2-methylperhydrocyclopenta[c]pyrrol-5-yl)-7H-pyrrolo[2,3-d]pyrimidine

Ausbeute 45.7%

Lösungsmittel

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe solvent was removed under reduced pressure
2. 2
   Sonstigethe residue was partitioned between dichloromethane (30 ml) and water (10 ml)
3. 3
   WaschenThe organic layer was washed with saturated aqueous sodium chloride (10 ml)
4. 4
   Trocknenthen dried over magnesium sulfate
5. 5
   Filtrationthen filtered
6. 6
   Sonstigethe filtrate evaporated under reduced pressure
7. 7
   Sonstigeto give a residue
8. 8
   SonstigeThe residue was purified by flash chromatography on silica

Vorschrift

A mixture of 4-chloro-5-iodo-7H-pyrrolo[2,3-d]pyrimidine (0.38 g, 1.36 mmol), 2-methylperhydrocyclopenta[c]pyrrol-5-ol (0.23 g, 1.63 mmol) and triphenylphosphine (0.71 g, 2.72 mmol) in tetrahydrofuran (20 mL) was treated with diethylazodicarboxylate (0.474 g, 2.72 mmol) and stirred for 2 hours at ambient temperature. The solvent was removed under reduced pressure and the residue was partitioned between dichloromethane (30 ml) and water (10 ml). The organic layer was washed with saturated aqueous sodium chloride (10 ml) then dried over magnesium sulfate then filtered and the filtrate evaporated under reduced pressure to give a residue. The residue was purified by flash chromatography on silica using dichloromethane/methanol (8:2) as mobile phase to yield 4-chloro-5-iodo-7-(2-methylperhydrocyclopenta[c]pyrrol-5-yl)-7H-pyrrolo[2,3-d]pyrimidine (0.25 g): 1H NMR (DMSO-d6, 400 MHz) δ 8.62 (s, 1H), 7.44 (s, 1H), 7.26 (s, 2H), 5.36 (m, 1H), 2.88 (m, 2H), 2.68 (m, 2H), 2.43 (m, 2H), 2.36 (s, 3H), 2.06-2.02 (m, 4H); TLC (dichloromethane/methanol 8:2) Rf =0.29; RP-HPLC (Hypersil HS C18, 5 μm, 100 A, 250×4.6 mm; 25-100% acetonitrile-0.1 M ammonium acetate over 10 min, 1 ml/min) tr=6.50 min; MS: MH+403.

Quelle