Cesium carbonate → 4-(4-chloro-5H-pyrrolo[3,2-d]pyrimidin-5-yl)butyl acetate

HRID 1786969Notes

Reaction equation

HRID 1786969 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+].[C:17]([O:20][CH2:21][CH2:22][CH2:23][CH2:24]Br)(=[O:19])[CH3:18].C(=O)([O-])O.[Na+]>CN(C)C=O>[C:17]([O:20][CH2:21][CH2:22][CH2:23][CH2:24][N:10]1[C:3]2[C:2]([Cl:1])=[N:7][CH:6]=[N:5][C:4]=2[CH:8]=[CH:9]1)(=[O:19])[CH3:18]

Participants

6

Reactant 4

HCID 10796Cesium carbonateHCID 784911-Butanol, 4-bromo-, 1-acetateHCID 516892Sodium BicarbonateHCID 53706954-chloro-5H-pyrrolo[3,2-d]pyrimidine

Product 1

HCID 866157664-(4-chloro-5H-pyrrolo[3,2-d]pyrimidin-5-yl)butyl acetateYield 81%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of 4-chloro-5H-pyrrolo[3,2-d]pyrimidine (0.768 g) in N,N-dimethylformamide (10 mL) was added cesium carbonate (2.01 g) under ice-cooling, and the reaction mixture was stirred while warming to room temperature for 15 min. 4-Bromobutyl acetate (1.26 g) was added dropwise to the reaction mixture, and the mixture was stirred at room temperature for 30 hrs. The reaction mixture was poured into 5% aqueous sodium hydrogen carbonate solution (80 mL), and extracted with ethyl acetate (100 mL×3). The organic layer washed successively with water and saturated brine and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the obtained residue was subjected to silica gel chromatography (eluent:hexane/ethyl acetate=95/5→0/100). The object fraction was concentrated under reduced pressure and dried to give the title compound (1.084 g) as a colorless transparent oil.

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred at room temperature for 30 hrs
  3. extractionextracted with ethyl acetate (100 mL×3)
  4. washThe organic layer washed successively with water and saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. concentrationThe object fraction was concentrated under reduced pressure
  8. customdried

Sources & evidence

ORD record
ord-fb2a9f88bfa54bb89323fc87d4e34de6
Source dataset
uspto-grants-2009_03
Patent number
US07507740B2

Reaction notes

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