Tributylstannane → 6-chloro-9-[(6aR,8R,9aS)-2,2,4,4-tetraisopropylhexahydrocyclopenta[f][1,3,5,2,4]trioxadisilocin-8-yl]-9H-purine

HRID 552732Notes

Reaction equation

HRID 552732 reaction equation
C(=S)(OC1C=CC=CC=1)O[C@@H:3]1[C@@H:7]2[O:8][Si:9]([CH:23]([CH3:25])[CH3:24])([CH:20]([CH3:22])[CH3:21])[O:10][Si:11]([CH:17]([CH3:19])[CH3:18])([CH:14]([CH3:16])[CH3:15])[O:12][CH2:13][C@H:6]2[CH2:5][C@H:4]1[N:26]1[CH:34]=[N:33][C:32]2[C:27]1=[N:28][CH:29]=[N:30][C:31]=2[Cl:35].C([SnH](CCCC)CCCC)CCC.N(C(C)(C)C#N)=NC(C)(C)C#N>C1(C)C=CC=CC=1>[Cl:35][C:31]1[N:30]=[CH:29][N:28]=[C:27]2[C:32]=1[N:33]=[CH:34][N:26]2[C@H:4]1[CH2:3][C@@H:7]2[O:8][Si:9]([CH:20]([CH3:22])[CH3:21])([CH:23]([CH3:25])[CH3:24])[O:10][Si:11]([CH:17]([CH3:18])[CH3:19])([CH:14]([CH3:15])[CH3:16])[O:12][CH2:13][C@H:6]2[CH2:5]1

Participants

5

Reactant 3

HCID 5948TributylstannaneHCID 6547AzobisisobutyronitrileHCID 86607321O-[(6aR,8R,9S,9aR)-8-(6-chloro-9H-purin-9-yl)-2,2,4,4-tetraisopropylhexahydrocyclopenta[f][1,3,5,2,4]trioxadisilocin-9-yl] O-phenyl thiocarbonate

Product 1

HCID 866073206-chloro-9-[(6aR,8R,9aS)-2,2,4,4-tetraisopropylhexahydrocyclopenta[f][1,3,5,2,4]trioxadisilocin-8-yl]-9H-purineYield 74%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of O-[(6aR,8R,9S,9aR)-8-(6-chloro-9H-purin-9-yl)-2,2,4,4-tetraisopropylhexahydrocyclopenta[f][1,3,5,2,4]trioxadisilocin-9-yl] O-phenyl thiocarbonate (0.851 g, 1.28 mol) in toluene (20 mL) was added tri-n-butyltin hydride (0.680 mL, 2.53 mmol) and 2,2′-azo-bis-isobutyronitrile (0.075 g, 0.46 mmol). This solution was refluxed for 1 h. The reaction mixture was concentrated and purified by flash chromatography (0 to 50% EtOAc/hexanes) to afford the title compound (0.14 g, 74%).

Workup

  1. temperatureThis solution was refluxed for 1 h
  2. concentrationThe reaction mixture was concentrated
  3. custompurified by flash chromatography (0 to 50% EtOAc/hexanes)

Sources & evidence

ORD record
ord-bd5dd8ba86404fffa470655b4fdd5745
Source dataset
uspto-grants-2011_05
Patent number
US07951810B2

Reaction notes

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