Reaction #79844

Reaction equation

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

Solvents

THF

Conditions

Workup

1. 1
   Otherthe 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
   Washwashed with EtOAc (2×50 mL)
5. 5
   Otherdried in vacuo

Procedure

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.

Source