Reaktion #79844

Reaktionsgleichung

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

1,4-dioxaspiro[4.5]decan-8-ol

triphenylphosphine

diethylazodicarboxylate

→

4-chloro-7-(1,4-dioxaspiro[4.5]dec-8-yl)-5-iodo-7H-pyrrolo[2,3-d]pyrimidine

Lösungsmittel

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigethe majority of solvent was then evaporated (250 mL remaining)
2. 2
   workup.ADDITIONEtOAc (450 mL) was then added
3. 3
   Filtrationthe resulting solid was filtered
4. 4
   Waschenwashed with EtOAc (2×50 mL)
5. 5
   Sonstigedried in vacuo

Vorschrift

To a solution of 4-chloro-5-iodo-7H-pyrrolo[2,3-d]pyrimidine (25.0 g, 0.09 mol), 1,4-dioxaspiro[4.5]decan-8-ol (35.8 g, 0.0267 mol) and triphenylphosphine (46.7 g, 0.178 mol) in THF (1.2 L) was added diethylazodicarboxylate (30.9 g, 0.178 mol) under nitrogen. The solution was stirred for 20 hr and the majority of solvent was then evaporated (250 mL remaining). EtOAc (450 mL) was then added and the resulting solid was filtered, washed with EtOAc (2×50 mL) and dried in vacuo to give 4-chloro-7-(1,4-dioxaspiro[4.5]dec-8-yl)-5-iodo-7H-pyrrolo[2,3-d]pyrimidine (22.5 g, 60%) as a cream solid. 1H NMR (d6 DMSO, 400 MHz) 8.64(1H, s), 8.10(1H, s), 4.74(1H, m), 3.90(4H, m), 2.12(2H, m), 1.91(2H, m), 1,71-1.83(4H, m). Rf in 1:4 EtOAc:heptane=0.12.

Quelle