Azido(trimethyl)stannane → HCID 178440122, compound

HRID 1708403Notes

Reaction equation

HRID 1708403 reaction equation
[CH2:1]([C:4]1[N:9]=[C:8]([CH3:10])[N:7]2[C:11](=O)[NH:12][N:13]=[C:6]2[C:5]=1[CH2:15][C:16]1[CH:21]=[CH:20][C:19]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[C:28]#[N:29])=[CH:18][CH:17]=1)[CH2:2][CH3:3].C[Sn]([N:34]=[N+:35]=[N-:36])(C)C>C1(C)C=CC=CC=1>[CH2:1]([C:4]1[N:9]=[C:8]([CH3:10])[N:7]2[CH:11]=[N:12][N:13]=[C:6]2[C:5]=1[CH2:15][C:16]1[CH:21]=[CH:20][C:19]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[C:28]2[NH:29][N:36]=[N:35][N:34]=2)=[CH:18][CH:17]=1)[CH2:2][CH3:3]

Participants

4

Reactant 2

HCID 5104973Azido(trimethyl)stannaneHCID 10091375HCID 10091375, compound

Product 1

HCID 178440122HCID 178440122, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

4 g of 7-n-propyl-5-methyl-8-[(2'-cyano-4-biphenylyl)methyl]-1,2,4-triazolo[4,3-c]pyrimidin-3(2H)-one, prepared in Example 15, are dissolved in 100 ml of toluene. 2.8 g of trimethyltin azide are added and the mixture is heated to reflux for 24 hours. The crystals formed are drained in the heated state and washed with ether, then suspended in 100 ml of tetrahydrofuran. Hydrogen chloride gas is bubbled into the mixture and, after the reactants have passed completely into solution, a precipitate appears. The mixture is left overnight at room temperature and the crystals formed are drained, washed with ether and dissolved in dilute sodium hydroxide solution. This solution is washed with ether, then acidified by bubbling in sulphur dioxide and extracted with chloroform. The organic phase is dried over magnesium sulphate and evaporated under vacuum, and the residue crystallises in an ether/acetone mixture to give 1.5 g of 7-n-propyl-5-methyl-8-{[2'-(5-tetrazolyl)-4-biphenylyl]methyl}-1,2,4-triazolo[4,3-c]pyrimidin-(3(2H)-one in the form of crystals of melting point 248°-249° C.

Workup

  1. temperaturethe mixture is heated
  2. temperatureto reflux for 24 hours
  3. customThe crystals formed
  4. washwashed with ether
  5. customHydrogen chloride gas is bubbled into the mixture
  6. customthe crystals formed
  7. washwashed with ether
  8. dissolutiondissolved in dilute sodium hydroxide solution
  9. washThis solution is washed with ether
  10. customby bubbling in sulphur dioxide
  11. extractionextracted with chloroform
  12. dry with materialThe organic phase is dried over magnesium sulphate
  13. customevaporated under vacuum
  14. customthe residue crystallises in an ether/acetone mixture

Sources & evidence

ORD record
ord-7dbbf46242124091a3c06331f5ee3388
Source dataset
uspto-grants-1994_10
Patent number
US05358950

Reaction notes

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