Cesium carbonate → HCID 86084735, compound

HRID 1786914Notes

Reaction equation

HRID 1786914 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][O:20][CH2:21][CH2:22][O:23][CH2:24][CH3:25]>CN(C)C=O.O>[Cl:1][C:2]1[C:3]2[N:10]([CH2:18][CH2:19][O:20][CH2:21][CH2:22][O:23][CH2:24][CH3:25])[CH:9]=[CH:8][C:4]=2[N:5]=[CH:6][N:7]=1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 53706954-chloro-5H-pyrrolo[3,2-d]pyrimidineHCID 70153241-Bromo-2-(2-ethoxyethoxy)ethane

Product 1

HCID 86084735HCID 86084735, compoundYield 83.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a suspension of 4-chloro-5H-pyrrolo[3,2-d]pyrimidine (300 mg) in N,N-dimethylformamide (2.0 mL) was added cesium carbonate (728 mg) under ice-cooling, and the mixture was stirred while warming to room temperature for 15 min. To the reaction mixture was added 1-bromo-2-(2-ethoxyethoxy)ethane (496 mg), and the mixture was stirred at room temperature for 20 hrs. The reaction mixture was diluted with water (20 mL) and extracted with ethyl acetate (20 mL×3). The organic layer washed with saturated brine (20 mL×3) and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the obtained residue was subjected to silica gel column-chromatography (silica gel, eluent:hexane/ethyl acetate=9/1→0/10). The object fraction was concentrated under reduced pressure and dried to give the title compound (440 mg) as a colorless transparent oil.

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred at room temperature for 20 hrs
  3. extractionextracted with ethyl acetate (20 mL×3)
  4. washThe organic layer washed with saturated brine (20 mL×3)
  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-067ac7b4543344aaa869db9cdbbb9194
Source dataset
uspto-grants-2009_03
Patent number
US07507740B2

Reaction notes

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