Ethylene Glycol → HCID 178488425, compound

HRID 1926928Notes

Reaction equation

HRID 1926928 reaction equation
[C:1]([CH2:3][CH2:4][O:5][CH2:6][CH2:7][CH2:8][O:9][C:10]1[C:11]2[C:18]([C:19]3[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=3)=[C:17]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[O:16][C:12]=2[N:13]=[CH:14][N:15]=1)#[N:2].C[Si]([N:37]=[N+:38]=[N-:39])(C)C.C([Sn](=O)CCCC)CCC.C(O)CO>C1(C)C=CC=CC=1>[CH3:26][O:25][C:22]1[CH:21]=[CH:20][C:19]([C:18]2[C:11]3[C:10]([O:9][CH2:8][CH2:7][CH2:6][O:5][CH2:4][CH2:3][C:1]4[NH:39][N:38]=[N:37][N:2]=4)=[N:15][CH:14]=[N:13][C:12]=3[O:16][C:17]=2[C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[CH:24][CH:23]=1

Participants

6

Reactant 4

HCID 174Ethylene GlycolHCID 61221Dibutyltin oxideHCID 78378AzidotrimethylsilaneHCID 58016794HCID 58016794, compound

Product 1

HCID 178488425HCID 178488425, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Stir 200 mg (0.47 mmol) 4-[3-(2-cyanoethoxy)propoxy]-5-(4-methoxyphenyl)-6-phenylfuro[2,3-d]-pyrimidine, 804 mg (7.0 mmol) trimethylsilylazide and 174 mg (0.70 mmol) di-n-butyltin oxide in 10 ml toluene overnight at 80° C. Concentrate the mixture by evaporation, take up the residue in water and acidify with dilute hydrochloric acid. Next, extract with methylene chloride. Wash the organic extracts with sodium chloride solution, dry over magnesium sulphate and concentrate by evaporation. Purify the residue that remains by RP-HPLC (column: Gromsil 250 mm×30 mm, 10 μm; acetonitrile/water gradient: 0-3 min 5% acetonitrile, 3-50 min 5%→98% acetonitrile, 50-55 min 98% acetonitrile). To remove organotin compounds, dissolve the beige foam obtained in 10 ml toluene and add 1 ml ethylene glycol. After heating for 1 h under reflux, remove the solvent under vacuum. Dissolve the residue in methylene chloride, wash with dilute hydrochloric acid and with sodium chloride solution, dry, and concentrate by evaporation. Purification of the residue by RP-HPLC (column: Gromsil 250 mm×30 mm, 10 μm; acetonitrile/water gradient: 0-3 min 5% acetonitrile, 3-34 min 5%→98% acetonitrile, 34-38 min 98% acetonitrile) gives 46 mg (21% of theor.) of the title compound as a beige foam.

Workup

  1. concentrationConcentrate the mixture
  2. customby evaporation
  3. extractionNext, extract with methylene chloride
  4. washWash the organic extracts with sodium chloride solution
  5. dry with materialdry over magnesium sulphate
  6. concentrationconcentrate by evaporation
  7. customPurify the residue
  8. customthat remains by RP-HPLC (column: Gromsil 250 mm×30 mm, 10 μm; acetonitrile/water gradient: 0-3 min 5% acetonitrile, 3-50 min 5%→98% acetonitrile, 50-55 min 98% acetonitrile)
  9. customTo remove organotin compounds
  10. dissolutiondissolve the beige foam
  11. customobtained in 10 ml toluene
  12. temperatureAfter heating for 1 h
  13. temperatureunder reflux
  14. customremove the solvent under vacuum
  15. dissolutionDissolve the residue in methylene chloride
  16. washwash with dilute hydrochloric acid and with sodium chloride solution
  17. customdry
  18. concentrationconcentrate by evaporation
  19. customPurification of the residue by RP-HPLC (column: Gromsil 250 mm×30 mm, 10 μm; acetonitrile/water gradient: 0-3 min 5% acetonitrile, 3-34 min 5%→98% acetonitrile, 34-38 min 98% acetonitrile)

Sources & evidence

ORD record
ord-869bd5600118426aa95d5a7fef9bc6c2
Source dataset
uspto-grants-2012_05
Patent number
US08183246B2

Reaction notes

Loading…