Triethylamine → HCID 13590356, compound

HRID 1380058Notes

Reaction equation

HRID 1380058 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:8]2[N:13]3[N:14]=[C:15]([NH2:17])[N:16]=[C:12]3[CH:11]=[CH:10][N:9]=2)[CH:5]=[CH:6][CH:7]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:24](N(CC)CC)[CH3:25]>CO>[C:24]([C:2]1[CH:3]=[C:4]([C:8]2[N:13]3[N:14]=[C:15]([NH2:17])[N:16]=[C:12]3[CH:11]=[CH:10][N:9]=2)[CH:5]=[CH:6][CH:7]=1)#[CH:25]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 11430Potassium CarbonateHCID 13590343HCID 13590343, compound

Product 1

HCID 13590356HCID 13590356, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A suspension of 2.0 g of 5-(3-bromophenyl) [1,2,4]triazolo[1,5-c]pyrimidin-2-amine in 45 ml of triethylamine was flushed with argon and stirred 15 minutes. A 17 mg portion of palladium II acetate and 34 mg of triphenyl phosphine were added followed by 1.06 g of ethynyl trimethylsilane. The mixture was heated to reflux, then allowed to stand overnight under argon, then again heated at reflux for 5 hours and then cooled. A 34 mg portion of palladium II acetate, 68 mg of triphenyl phosphine and 2.12 g of ethynyl trimethylsilane were added and this mixture was refluxed 15 hours. The mixture was cooled, evaporated, taken up in 200 ml of chloroform, washed with 100 ml of saturated aqueous potassium bicarbonate, dried, filtered and evaporated giving a brown glass. This glass was taken up in 50 ml of methanol and 200 mg. of anhydrous potassium carbonate were added. This mixture was sealed, stirred overnignt and then evaporated. The residue was taken up in 100 ml of chloroform, washed with 50 ml of dilute aqueous potassium bicarbonate, dried, filtered through hydrous magnesium silicate and evaporated. This solid was crystallized from chloroform-cyclohexane, giving 300 mg of the desired product, mp 170°-172° C.

Workup

  1. customwas flushed with argon
  2. additionA 17 mg portion of palladium II acetate and 34 mg of triphenyl phosphine were added
  3. temperatureThe mixture was heated
  4. temperatureto reflux
  5. waitto stand overnight under argon
  6. temperatureagain heated
  7. temperatureat reflux for 5 hours
  8. temperaturecooled
  9. additionA 34 mg portion of palladium II acetate, 68 mg of triphenyl phosphine and 2.12 g of ethynyl trimethylsilane were added
  10. temperaturethis mixture was refluxed 15 hours
  11. temperatureThe mixture was cooled
  12. customevaporated
  13. washwashed with 100 ml of saturated aqueous potassium bicarbonate
  14. customdried
  15. filtrationfiltered
  16. customevaporated
  17. customgiving a brown glass
  18. customThis mixture was sealed
  19. stirringstirred overnignt
  20. customevaporated
  21. washwashed with 50 ml of dilute aqueous potassium bicarbonate
  22. customdried
  23. filtrationfiltered through hydrous magnesium silicate
  24. customevaporated
  25. customThis solid was crystallized from chloroform-cyclohexane

Sources & evidence

ORD record
ord-3d91e15807804ad48072da65f0032488
Source dataset
uspto-grants-1986_04
Patent number
US04579848

Reaction notes

Loading…