Ethyl Acetate → 5-Bromo-2,4-dichloro-7H-pyrrolo[2,3-d]pyrimidine

HRID 2046990Notes

Reaction equation

HRID 2046990 reaction equation
[Cl:1][C:2]1[N:3]=[C:4]([Cl:11])[C:5]2[CH:10]=[CH:9][NH:8][C:6]=2[N:7]=1.[Br:12]Br.CCOC(C)=O.[O-]S([O-])=O.[Na+].[Na+]>O1CCOCC1>[Br:12][C:10]1[C:5]2[C:4]([Cl:11])=[N:3][C:2]([Cl:1])=[N:7][C:6]=2[NH:8][CH:9]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 24408BromineHCID 24437Sodium SulfiteHCID 141168712,4-Dichloro-7H-pyrrolo[2,3-d]pyrimidine

Product 1

HCID 579904405-Bromo-2,4-dichloro-7H-pyrrolo[2,3-d]pyrimidine

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
0 °C

Procedure

To 935 mg 2,4-dichloro-7H-pyrrolo[2,3-d]pyrimidine (3a) (5.0 mmol) in 100 mL of 1,4-dioxane was slowly added 256 μL of Br2 (5.0 mmol) at 0° C. over a period of 10 minutes. After stirring for 30 minutes at 0° C., the reaction mixture was poured into a mixture of 150 mL of EtOAc and 150 mL of saturated aqueous Na2SO3 then filtered through celite. The aqueous phase was extracted with EtOAc (3×100 mL) and combined organic layers were washed with brine, concentrated and purified by flash column chromatography to give the title compound.

Workup

  1. customat 0° C.
  2. customof 10 minutes
  3. filtrationthen filtered through celite
  4. extractionThe aqueous phase was extracted with EtOAc (3×100 mL)
  5. washwere washed with brine
  6. concentrationconcentrated
  7. custompurified by flash column chromatography

Sources & evidence

ORD record
ord-b83c6fe820a742e9850de173c7b4e46a
Source dataset
uspto-grants-2013_11
Patent number
US08592432B2

Reaction notes

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