Tributyltin Chloride → HCID 178441568, compound

HRID 2393062Notes

Reaction equation

HRID 2393062 reaction equation
[CH2:1]([C:5]1[N:6]=[C:7]2[NH:29][C:28](=[O:30])[CH:27]([CH3:31])[N:8]2[C:9](=[O:26])[C:10]=1[CH2:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[C:24]#[N:25])=[CH:14][CH:13]=1)[CH2:2][CH2:3][CH3:4].[N-:32]=[N+:33]=[N-:34].[Na+].C([Sn](Cl)(CCCC)CCCC)CCC>C1(C)C=CC=CC=1.CN(C=O)C>[CH2:1]([C:5]1[N:6]=[C:7]2[NH:29][C:28](=[O:30])[CH:27]([CH3:31])[N:8]2[C:9](=[O:26])[C:10]=1[CH2:11][C:12]1[CH:13]=[CH:14][C:15]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[C:24]2[NH:34][N:33]=[N:32][N:25]=2)=[CH:16][CH:17]=1)[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 3

HCID 15096Tributyltin ChlorideHCID 33557Sodium AzideHCID 136098646HCID 136098646, compound

Product 1

HCID 178441568HCID 178441568, compoundYield 45%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 0.2 g of 7-butyl-6-((2'-cyanobiphenyl-4-yl)methyl]-3-methylimidazo[1,2-a]pyrimidin-2,5-dione in 4 ml of toluene and 1 ml of DMF is added with 38 mg of sodium azide and 0.17 ml of tributylstannyl chloride. After 72 h under reflux, the solvent is evaporated under reduced pressure and the residue is taken up in a NaOH diluted solution and extracted with toluene. The aqueous phase is acidified to pH 5 with AcOH, to separate a white solid which is filtered off and washed first with H2O, and then with a mixture of hexane-toluene to obtain g 0.1 of a white solid, after crystallization (45% yield).

Workup

  1. temperatureAfter 72 h under reflux
  2. customthe solvent is evaporated under reduced pressure
  3. extractionextracted with toluene
  4. customto separate a white solid which
  5. filtrationis filtered off
  6. washwashed first with H2O
  7. additionwith a mixture of hexane-toluene
  8. customto obtain
  9. customafter crystallization (45% yield)

Sources & evidence

ORD record
ord-0f854cbdd5244455a72eee8150c9dc53
Source dataset
uspto-grants-1998_09
Patent number
US05804583

Reaction notes

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