Bromine → 5-bromo-7H-pyrrolo[2,3-d]pyrimidine

HRID 1527253Notes

Reaction equation

HRID 1527253 reaction equation
[Br:1]Br.[N:3]1[C:8]2[NH:9][CH:10]=[CH:11][C:7]=2[CH:6]=[N:5][CH:4]=1.[O-]S([O-])(=S)=O.[Na+].[Na+].C([O-])(O)=O.[Na+]>CN(C=O)C.O>[Br:1][C:11]1[C:7]2[CH:6]=[N:5][CH:4]=[N:3][C:8]=2[NH:9][CH:10]=1

Participants

7

Reactant 4

HCID 24408BromineHCID 24477Sodium ThiosulfateHCID 2615917H-Pyrrolo(2,3-d)pyrimidineHCID 516892Sodium Bicarbonate

Product 1

HCID 107980055-bromo-7H-pyrrolo[2,3-d]pyrimidine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

A solution of bromine (0.086 mL, 1.68 mmol) in DMF (5.5 mL) was added to a solution of 7H-pyrrolo[2,3-d]pyrimidine (200 mg, 1.68 mmol) in DMF (5.5 mL). The reaction mixture was stirred at RT for 4 h and poured into a mixture of ice and water containing Na2S2O3. A saturated aqueous solution of NaHCO3 was added (until basic pH), the layers were separated and the aqueous layer was extracted twice with EtOAc. The combined organic extracts were washed with brine, dried (Na2SO4), filtered and concentrated. The material thus obtained was used without further purification in the next step. TLC, Rf (CH2Cl2/MeOH 9:1)=0.45; MS (UPLC/MS): 198.1/200.1 [M+H]+, 196.1/198.1 [M−H]−.

Workup

  1. customthe layers were separated
  2. extractionthe aqueous layer was extracted twice with EtOAc
  3. washThe combined organic extracts were washed with brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe material thus obtained
  8. customwas used without further purification in the next step

Sources & evidence

ORD record
ord-bad875e7134b48638aeda43002ae52a8
Source dataset
uspto-grants-2015_07
Patent number
US09085555B2

Reaction notes

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