Reaction #1458445

Reaction equation

4-Chloro-7H-pyrrolo[2,3-d]pyrimidine

N-iodosuccinimide

→

title compound

Yield 74.6%

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

Yield 74.6%

Solvents

DMF

Conditions

Workup

1. 1
   workup.WAITleft at ambient temperature in the darkness over night
2. 2
   OtherThe solvent was evaporated
3. 3
   Filtrationfiltered
4. 4
   Washwashed twice with hot water
5. 5
   Othercrystallized from ethanol

Procedure

4-Chloro-7H-pyrrolo[2,3-d]pyrimidine 10.75 g (70 mmol) (Toronto Research Chemicals, Inc) and N-iodosuccinimide (16.8 g, 75 mmol) were dissolved in 400 mL of dry DMF and left at ambient temperature in the darkness over night. The solvent was evaporated. The yellow residue was suspended in hot 10% solution of Na2SO3, filtered, washed twice with hot water and crystallized from ethanol to yield 14.6 g (74.6%) of the title compound as off-white crystals. The mother liquid was evaporated up to ⅓ volume and crystallized again from ethanol to give 2.47 g (12.3%) of the title product.

Source