反応 #79808

反応方程式

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

収率 45.7%

溶媒

tetrahydrofuran

反応条件

後処理

1. 1
   その他The solvent was removed under reduced pressure
2. 2
   その他the residue was partitioned between dichloromethane (30 ml) and water (10 ml)
3. 3
   洗浄The organic layer was washed with saturated aqueous sodium chloride (10 ml)
4. 4
   乾燥then dried over magnesium sulfate
5. 5
   ろ過then filtered
6. 6
   その他the filtrate evaporated under reduced pressure
7. 7
   その他to give a residue
8. 8
   その他The residue was purified by flash chromatography on silica

実験手順

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.

出典