Iodoethane → 4-Chloro-5-ethyl-5H-pyrrolo[3,2-d]pyrimidine

HRID 1786887Notes

Reaction equation

HRID 1786887 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-].[K+].[K+].I[CH2:18][CH3:19]>CN(C)C=O.O>[Cl:1][C:2]1[C:3]2[N:10]([CH2:18][CH3:19])[CH:9]=[CH:8][C:4]=2[N:5]=[CH:6][N:7]=1

Participants

6

Reactant 3

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 53706954-chloro-5H-pyrrolo[3,2-d]pyrimidine

Product 1

HCID 714134604-Chloro-5-ethyl-5H-pyrrolo[3,2-d]pyrimidineYield 79.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a suspension of 4-chloro-5H-pyrrolo[3,2-d]pyrimidine (200 mg) in N,N-dimethylformamide (1.3 mL) was added potassium carbonate (269 mg) under ice-cooling, and the mixture was stirred while warming to room temperature for 15 min. Iodoethane (305 mg) was added to the reaction mixture, and the mixture was stirred at room temperature for 3 hrs. The reaction mixture was diluted with water (20 mL) and extracted with ethyl acetate (30 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=80/20→10/90). The object fraction was concentrated under reduced pressure and dried to give the title compound (187 mg) as a pale-yellow solid.

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred at room temperature for 3 hrs
  3. extractionextracted with ethyl acetate (30 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-5d84124ecc41478eb68773bd82261c72
Source dataset
uspto-grants-2009_03
Patent number
US07507740B2

Reaction notes

Loading…