Allyl bromide → 5-allyl-4-chloro-5H-pyrrolo[3,2-d]pyrimidine

HRID 244448Notes

Reaction equation

HRID 244448 reaction equation
[Cl:1][C:2]1[C:3]2[NH:10][CH:9]=[CH:8][C:4]=2[N:5]=[CH:6][N:7]=1.[CH2:11](Br)[CH:12]=[CH2:13].[H-].[Na+]>CN(C=O)C>[CH2:13]([N:10]1[C:3]2[C:2]([Cl:1])=[N:7][CH:6]=[N:5][C:4]=2[CH:8]=[CH:9]1)[CH:12]=[CH2:11]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 24758Sodium hydrideHCID 53706954-chloro-5H-pyrrolo[3,2-d]pyrimidine

Product 1

HCID 594373215-allyl-4-chloro-5H-pyrrolo[3,2-d]pyrimidineYield 88%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a room temperature solution of 4-chloro-5H-pyrrolo[3,2-d]pyrimidine (1.2 g, 7.8 mmol,) and allyl bromide in 40 mL of DMF was added 60% sodium hydride (625 mg, 15.6 mmol, 2 equiv.) in several portions. After 20 minutes, the reaction was quenched with water and extracted with EtOAc. The combined organics were dried, filtered, and concentrated in vacuo. The residue was purified by flash chromatography (20% EtOAc/hexanes) to provide 1.3 g (88%) of 5-allyl-4-chloro-5H-pyrrolo[3,2-d]pyrimidine as a yellow oil which was used without further purification.

Workup

  1. customthe reaction was quenched with water
  2. extractionextracted with EtOAc
  3. customThe combined organics were dried
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash chromatography (20% EtOAc/hexanes)

Sources & evidence

ORD record
ord-2d20aa6a7e6d4c8eabbe5288d3bdc54c
Source dataset
uspto-grants-2014_02
Patent number
US08658637B2

Reaction notes

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