Iodoethane → HCID 67520938, compound

HRID 1786870Notes

Reaction equation

HRID 1786870 reaction equation
[Si:1]([O:8][CH2:9]/[CH:10]=[CH:11]/[C:12]1[NH:20][C:19]2[C:18]([O:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[N:17][CH:16]=[N:15][C:14]=2[CH:13]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C(=O)([O-])[O-].[Cs+].[Cs+].I[CH2:35][CH3:36]>CN(C)C=O.C(OCC)(=O)C>[Si:1]([O:8][CH2:9]/[CH:10]=[CH:11]/[C:12]1[N:20]([CH2:35][CH3:36])[C:19]2[C:18]([O:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[N:17][CH:16]=[N:15][C:14]=2[CH:13]=1)([C:4]([CH3:7])([CH3:5])[CH3:6])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 6340IodoethaneHCID 10796Cesium carbonateHCID 67520300HCID 67520300, compound

Product 1

HCID 67520938HCID 67520938, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

6-((1E)-3-{[tert-Butyl(dimethyl)silyl]oxy}-1-propenyl)-4-phenoxy-5H-pyrrolo[3,2-d]pyrimidine (100 mg) was dissolved in N,N-dimethylformamide (0.786 mL), cesium carbonate (102.6 mg) was added, and the mixture was stirred at room temperature for 20 min. Iodoethane (0.0231 mL) was added and the mixture was stirred at room temperature for 2 hrs and at 40° C. for 4 hrs. After cooling to room temperature, the reaction mixture was diluted with ethyl acetate (50 mL) and washed successively with water (30 mL) and saturated brine (30 mL). The organic layer was dried over magnesium sulfate and concentrated under reduced pressure. The residue was separated and purified by silica gel column chromatography (eluent, hexane:ethyl acetate=80:20→50:50) to give the title compound (79 mg) as an oil.

Workup

  1. stirringthe mixture was stirred at room temperature for 2 hrs and at 40° C. for 4 hrs
  2. temperatureAfter cooling to room temperature
  3. washwashed successively with water (30 mL) and saturated brine (30 mL)
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was separated
  7. custompurified by silica gel column chromatography (eluent, hexane:ethyl acetate=80:20→50:50)

Sources & evidence

ORD record
ord-ad3b6a294f744dfd8cf1500c0e64560d
Source dataset
uspto-grants-2009_03
Patent number
US07507740B2

Reaction notes

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