Tributyltin azide → HCID 178518713, compound

HRID 566387Notes

Reaction equation

HRID 566387 reaction equation
[C:1]([C:3]1[N:13]=[CH:12][C:6]2[N:7]=[CH:8][NH:9][C:10](=[O:11])[C:5]=2[CH:4]=1)#[N:2].C([Sn]([N:27]=[N+:28]=[N-:29])(CCCC)CCCC)CCC>COCCOCCOC>[NH:27]1[C:1]([C:3]2[N:13]=[CH:12][C:6]3[N:7]=[CH:8][NH:9][C:10](=[O:11])[C:5]=3[CH:4]=2)=[N:2][N:29]=[N:28]1

Participants

4

Reactant 2

HCID 4984872Tributyltin azideHCID 1358174456-Cyano-pyrido[3,4-d]pyrimidin-4-one

Product 1

HCID 178518713HCID 178518713, compoundYield 440.9%

Reagents, catalysts & solvents 1

HCID 8150DiglymeSolvent

Procedure

6-Cyano-pyrido[3,4-d]pyrimidin-4-one (0.3 g) in diglyme (2 ml) was treated with tributyl tin azide (0.49 g) at reflux under N2 for 15 hours. The cooled mixture was partitioned between ethyl acetate and water and the aqueous phase extracted further with ethyl acetate. The aqueous phase was concentrated in vacuo, the residue taken up in methanol and inorganics removed by filtration. Subsequent concentration gave the title compound (1.4 g) as a beige solid; δH [2H6]DMSO 8.96 (1H,s), 8.50 (1H,s), 8.27 (1H,s); m/z (M+1+)216.

Workup

  1. temperatureat reflux under N2 for 15 hours
  2. customThe cooled mixture was partitioned between ethyl acetate and water
  3. extractionthe aqueous phase extracted further with ethyl acetate
  4. concentrationThe aqueous phase was concentrated in vacuo
  5. custominorganics removed by filtration
  6. concentrationSubsequent concentration

Sources & evidence

ORD record
ord-546472f73e6147b7bb2a9711824449a9
Source dataset
uspto-grants-2001_01
Patent number
US06174889B1

Reaction notes

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