Reacción #79808

Ecuación de reacción

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

Rendimiento 45.7%

Disolventes

tetrahydrofuran

Condiciones de reacción

Tratamiento posterior

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

Procedimiento

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.

Fuente