반응 #79808

반응 방정식

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

수율 45.7%

용매

tetrahydrofuran

반응 조건

후처리

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

실험 절차

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.

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