Water → 4-chloro-5-(3-chloropropyl)-5H-pyrrolo[3,2-d]pyrimidine

HRID 1787018Notes

Reaction equation

HRID 1787018 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.C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:18][CH2:19][CH2:20][Cl:21].O>CN(C)C=O>[Cl:1][C:2]1[C:3]2[N:10]([CH2:18][CH2:19][CH2:20][Cl:21])[CH:9]=[CH:8][C:4]=2[N:5]=[CH:6][N:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 80061-Bromo-3-chloropropaneHCID 10796Cesium carbonateHCID 53706954-chloro-5H-pyrrolo[3,2-d]pyrimidine

Product 1

HCID 860848304-chloro-5-(3-chloropropyl)-5H-pyrrolo[3,2-d]pyrimidineYield 81%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-chloro-5H-pyrrolo[3,2-d]pyrimidine (1.54 g) in N,N-dimethylformamide (20 mL) was added cesium carbonate (4.89 g) under ice-cooling, and the mixture was stirred under ice-cooling for 20 min. 1-Bromo-3-chloropropane (1.89 g) was added and the mixture was stirred under ice-cooling for 1 hr and at room temperature for 32 hrs. The reaction mixture was poured into water (40 mL), and the mixture was extracted with ethyl acetate (60 mL×2). The organic layers were combined, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent, hexane:ethyl acetate=80:20→50:50) to give the title compound (1.87 g).

Workup

  1. temperaturecooling
  2. temperaturecooling for 20 min
  3. stirringthe mixture was stirred under ice-
  4. extractionthe mixture was extracted with ethyl acetate (60 mL×2)
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (eluent, hexane:ethyl acetate=80:20→50:50)

Sources & evidence

ORD record
ord-20b9bc27794b4a318c30b0fc7a348295
Source dataset
uspto-grants-2009_03
Patent number
US07507740B2

Reaction notes

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