Tributylstannane → HCID 67687191, compound

HRID 129098Notes

Reaction equation

HRID 129098 reaction equation
[C:1]([CH:9]([OH:30])[C@H:10]1[O:14][C@@H:13]([N:15]2[CH:23]=[C:21]([CH3:22])[C:19](=[O:20])[NH:18][C:16]2=[O:17])[CH:12](Br)[C@:11]1([S:26]([CH3:29])(=[O:28])=[O:27])[OH:25])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CCCC[SnH](CCCC)CCCC.CC(N=NC(C#N)(C)C)(C#N)C>>[C:1]([CH:9]([OH:30])[C@H:10]1[O:14][C@@H:13]([N:15]2[CH:23]=[C:21]([CH3:22])[C:19](=[O:20])[NH:18][C:16]2=[O:17])[CH2:12][C@:11]1([S:26]([CH3:29])(=[O:28])=[O:27])[OH:25])(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 5948TributylstannaneHCID 6547AzobisisobutyronitrileHCID 67687185HCID 67687185, compound

Product 1

HCID 67687191HCID 67687191, compound

Conditions

Temperature
25 °C

Procedure

To a 50 ml round-bottom flask equipped with condenser, nitrogen inlet, and thermometer was added 5'-benzoyl-3'-methanesulfonyl-2'-bromo-thymidine (5) (3.0 g, 5.96 mmol) and 30 ml of the specified solvent (see the table below). Bu3SnH (3.0 ml, 11.15 mmol; 1.9 equiv) was then added. The reaction mixture was heated to reflux or to the temperature specified in the table, to give a clear, homogeneous solution. The reaction mixture was then cooled slightly and 300 mg AIBN was added. The mixture was heated to reflux or the temperature specified in table for 45 minutes at which time the reaction was complete by HPLC (or for a period of time as specified in the table). The mixture was then cooled to 25° C. and concentrated to give a residue. The residue was purified by silica gel column chromatography (Kiesgel 60, 230-400 mesh silica gel, 2.5×23 cm column, 3/1 EtOAc/hexane as eluent) or by methylene chloride trituration to afford 5'-benzoyl-3'-methanesulfonylthymidine (6). These results were summarized in the table.

Workup

  1. customTo a 50 ml round-bottom flask equipped with condenser, nitrogen inlet
  2. temperatureThe reaction mixture was heated
  3. temperatureto reflux or to the temperature
  4. customto give a clear, homogeneous solution
  5. temperatureThe reaction mixture was then cooled slightly
  6. temperatureThe mixture was heated
  7. temperatureto reflux
  8. concentrationconcentrated
  9. customto give a residue
  10. customThe residue was purified by silica gel column chromatography (Kiesgel 60, 230-400 mesh silica gel, 2.5×23 cm column, 3/1 EtOAc/hexane as eluent) or by methylene chloride trituration

Sources & evidence

ORD record
ord-08d1b0f0948f46ed893b2379524ac04a
Source dataset
uspto-grants-1995_11
Patent number
US05466787

Reaction notes

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