N-Iodosuccinimide → HCID 178478409, compound

To a 250 ml round-bottomed flask, protected from light with aluminum foil, are added 4-chloro-7H-pyrrolo[2,3-d]pyrimidine 1 (2.15 g, 14.0 mmol) and N-iodosuccinimide (3.37 g, 14.98 mmol) dissolved in anhydrous DMF. The reaction mixture is stirred at room temperature under nitrogen for 16 hrs. The solvent is removed in vacuo, and the residue is dissolved in methylene chloride (250 ml). The reaction mixture is washed with brine (50 ml), and the organic layer is separated, dried over Na2SO4, and concentrated in vacuo. The crude residue is purified by flash-chromatography on silica gel and eluted with 60% EtOAc in cyclohexane. Fractions containing the desired product (TLC) are pooled and evaporated to afford 4-chloro-5-iodo-pyrrolo[2,3-d]pyrimidine as a pale-yellow solid.

1. customTo a 250 ml round-bottomed flask, protected
2. customThe solvent is removed in vacuo
3. dissolutionthe residue is dissolved in methylene chloride (250 ml)
4. washThe reaction mixture is washed with brine (50 ml)
5. customthe organic layer is separated
6. dry with materialdried over Na2SO4
7. concentrationconcentrated in vacuo
8. customThe crude residue is purified by flash-chromatography on silica gel
9. washeluted with 60% EtOAc in cyclohexane
10. additionFractions containing the desired product (TLC)
11. customevaporated

ORD record

ord-60b9a4d18aac4daf82bf67d2b6f5e56c

Source dataset

uspto-grants-2012_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08278282B2