Tributylvinyltin → HCID 67164220, compound

HRID 552767Notes

Reaction equation

HRID 552767 reaction equation
[Si:1]([O:8][CH2:9][C@@H:10]1[C@H:14]2[O:15][C:16]([CH3:19])([CH3:18])[O:17][C@H:13]2[C@H:12]([N:20]2[CH:28]=[N:27][C:26]3[C:21]2=[N:22][CH:23]=[N:24][C:25]=3Cl)[O:11]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[CH2:30]([Sn](CCCC)(CCCC)C=C)[CH2:31]CC>ClCCCl.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[Si:1]([O:8][CH2:9][C@@H:10]1[C@H:14]2[O:15][C:16]([CH3:19])([CH3:18])[O:17][C@H:13]2[C@H:12]([N:20]2[CH:28]=[N:27][C:26]3[C:21]2=[N:22][CH:23]=[N:24][C:25]=3[CH:30]=[CH2:31])[O:11]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 81998TributylvinyltinHCID 15101786HCID 15101786, compound

Product 1

HCID 67164220HCID 67164220, compoundYield 67.2%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 111,2-DichloroethaneSolvent

Procedure

To a solution of 9-[(3aR,4R,6R,6aR)-6-({[tert-butyl(dimethyl)silyl]oxy}methyl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl]-6-chloro-9H-purine (330 mg, 0.74 mmol) and tributyl(vinyl)stannane (0.26 mL, 0.88 mmol) in 1,2 dichloroethane (10 mL) was added Pd(Ph3P)2Cl2 (26 mg, 0.03 mmol) and the r×n mixture was heated at reflux overnight. The solvent was removed and the residue purified by flash chromatography (0 to 20% EtOAc/hexanes) to yield 215 mg (67%) of the title compound.

Workup

  1. temperaturethe r×n mixture was heated
  2. temperatureat reflux overnight
  3. customThe solvent was removed
  4. customthe residue purified by flash chromatography (0 to 20% EtOAc/hexanes)

Sources & evidence

ORD record
ord-9c14bbe1d7db4ba7a9383b9080c3a23f
Source dataset
uspto-grants-2011_05
Patent number
US07951810B2

Reaction notes

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