Triphenylphosphine → HCID 86619139, compound

HRID 2238650Notes

Reaction equation

HRID 2238650 reaction equation
[C:1]([O:3][CH2:4][CH3:5])#[CH:2].B.O1CCCC1.[Cl:12][C:13]1[N:21]=[C:20]2[C:16]([N:17]=[CH:18][N:19]2[CH2:22][O:23][CH2:24][CH2:25][Si:26]([CH3:29])([CH3:28])[CH3:27])=[C:15](Cl)[N:14]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[OH-].[Na+]>O1CCCC1.C(OCC)(=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[Cl:12][C:13]1[N:21]=[C:20]2[C:16]([N:17]=[CH:18][N:19]2[CH2:22][O:23][CH2:24][CH2:25][Si:26]([CH3:29])([CH3:28])[CH3:27])=[C:15](/[CH:2]=[CH:1]/[O:3][CH2:4][CH3:5])[N:14]=1

Participants

9

Reactant 5

HCID 11776TriphenylphosphineHCID 14798Sodium HydroxideHCID 61239Ether, ethyl ethynylHCID 2723981Borane;tetrahydrofuranHCID 582852322,6-Dichloro-9-((2-(trimethylsilyl)ethoxy)methyl)-9H-purine

Product 1

HCID 86619139HCID 86619139, compoundYield 20.3%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

2 g of ethyl ethynyl ether (50% v/v hexane solution) was dissolved in 20 mL of tetrahydrofuran, and 4.7 mL of borane-tetrahydrofuran complex (1.0M tetrahydrofuran solution) was added under an ice-cold condition. After stirring the mixture at room temperature for 3 hours, 50 mL of tetrahydrofuran, 3 g of 2,6-dichloro-9-{[2-(trimethylsilyl)ethoxy]methyl}-9H-purine [56-1], 222 mg of triphenylphosphine, 63 mg of palladium acetate, and 7.0 mL of 4N aqueous solution of sodium hydroxide were added, and the mixture was heated overnight under reflux. The reaction mixture was cooled back to room temperature, diluted with ethyl acetate, and then washed with water and saturated saline in the subsequent order. The obtained organic layer was dried over anhydrous magnesium sulfate. The insolubles were filtered, the filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography, to obtain 676 mg of 2-chloro-6-[(E)-2-ethoxyvinyl]-9-{[2-(trimethylsilyl)ethoxy]methyl}-9H-purine [56-2] as a light brown oily product.

Workup

  1. temperaturethe mixture was heated overnight
  2. temperatureunder reflux
  3. temperatureThe reaction mixture was cooled back to room temperature
  4. washwashed with water and saturated saline in the subsequent order
  5. dry with materialThe obtained organic layer was dried over anhydrous magnesium sulfate
  6. filtrationThe insolubles were filtered
  7. concentrationthe filtrate was concentrated under reduced pressure
  8. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-d61f86be39c54e8ba56991a77261d74d
Source dataset
uspto-grants-2010_05
Patent number
US07718801B2

Reaction notes

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