N-bromobutanimide → 5-allyl-7-bromo-4-chloro-5H-pyrrolo[3,2-d]pyrimidine

HRID 244449Notes

Reaction equation

HRID 244449 reaction equation
[CH2:1]([N:4]1[C:12]2[C:11]([Cl:13])=[N:10][CH:9]=[N:8][C:7]=2[CH:6]=[CH:5]1)[CH:2]=[CH2:3].[Br:14]N1C(=O)CCC1=O>C1COCC1>[CH2:1]([N:4]1[C:12]2[C:11]([Cl:13])=[N:10][CH:9]=[N:8][C:7]=2[C:6]([Br:14])=[CH:5]1)[CH:2]=[CH2:3]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 594373215-allyl-4-chloro-5H-pyrrolo[3,2-d]pyrimidine

Product 1

HCID 594373185-allyl-7-bromo-4-chloro-5H-pyrrolo[3,2-d]pyrimidineYield 93%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a room temperature solution of 5-allyl-4-chloro-5H-pyrrolo[3,2-d]pyrimidine (960 mg, 5 mmol, 1 equiv.) in 100 mL of THF was added N-bromosuccinimide (1.1 g, 6 mmol, 1.1 equiv.). After 1 hour, the THF was concentrated and the residue diluted with water and extracted with EtOAc. The combined organic layers were dried, filtered, and concentrated in vacuo. The solids were sonicated in water/saturated aqueous NaHCO3/MeOH and filtered to provide 1.26 g (93%) of 5-allyl-7-bromo-4-chloro-5H-pyrrolo[3,2-d]pyrimidine as an off-white solid which was used without further purification.

Workup

  1. concentrationthe THF was concentrated
  2. additionthe residue diluted with water
  3. extractionextracted with EtOAc
  4. customThe combined organic layers were dried
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe solids were sonicated in water/saturated aqueous NaHCO3/MeOH
  8. filtrationfiltered

Sources & evidence

ORD record
ord-090e498e3fb045fc89e093aa808929f6
Source dataset
uspto-grants-2014_02
Patent number
US08658637B2

Reaction notes

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