Ethyl Acrylate → ethyl 3-(4-chloro-5H-pyrrolo[3,2-d]pyrimidin-5-yl)propanoate

HRID 1787053Notes

Reaction equation

HRID 1787053 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:11]([O:15][CH2:16][CH3:17])(=[O:14])[CH:12]=[CH2:13].C(=O)([O-])[O-].[K+].[K+].[Cl-].[NH4+]>CN(C)C=O>[Cl:1][C:2]1[C:3]2[N:10]([CH2:13][CH2:12][C:11]([O:15][CH2:16][CH3:17])=[O:14])[CH:9]=[CH:8][C:4]=2[N:5]=[CH:6][N:7]=1

Participants

6

Reactant 4

HCID 8821Ethyl Acrylate3×HCID 11430Potassium Carbonate2×HCID 25517Ammonium ChlorideHCID 53706954-chloro-5H-pyrrolo[3,2-d]pyrimidine

Product 1

HCID 86084810ethyl 3-(4-chloro-5H-pyrrolo[3,2-d]pyrimidin-5-yl)propanoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-Chloro-5H-pyrrolo[3,2-d]pyrimidine (303 mg) was dissolved in N,N-dimethylformamide (9 mL), ethyl acrylate (0.3 mL) and potassium carbonate (538 mg) were sequentially added, and the mixture was stirred at room temperature for 7.5 hrs. Ethyl acrylate (0.2 mL) was added, and the mixture was stirred for 16 hrs. Ethyl acrylate (0.3 mL) and potassium carbonate (526 mg) were further added, and the mixture was stirred for 6 hrs. The reaction mixture was treated with saturated aqueous ammonium chloride solution and the mixture was extracted with ethyl acetate. The organic layer washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was separated and purified by silica gel column chromatography (eluent, hexane:ethyl acetate=66:34→20:80) to give the title compound (404 mg) as a colorless oil.

Workup

  1. stirringthe mixture was stirred for 16 hrs
  2. stirringthe mixture was stirred for 6 hrs
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was separated
  8. custompurified by silica gel column chromatography (eluent, hexane:ethyl acetate=66:34→20:80)

Sources & evidence

ORD record
ord-d02c53dd9aa349dfa54725c51b49d7d6
Source dataset
uspto-grants-2009_03
Patent number
US07507740B2

Reaction notes

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