3,5-Diamino-1,2,4-triazole → 7-(2-thienyl)[1,2,4]triazolo[1,5-a]pyrimidin-2-amine

HRID 1816941Notes

Reaction equation

HRID 1816941 reaction equation
[NH2:1][C:2]1[N:6]=[C:5]([NH2:7])[NH:4][N:3]=1.[C:8]12([CH2:18][S:19](O)(=O)=O)C(C)(C)[CH:12]([CH2:13][CH2:14]1)[CH2:11][C:9]2=O>C1(C)C=CC=CC=1>[S:19]1[CH:18]=[CH:8][CH:9]=[C:11]1[C:12]1[N:3]2[N:4]=[C:5]([NH2:7])[N:6]=[C:2]2[N:1]=[CH:14][CH:13]=1

Participants

4

Reactant 2

HCID 150783,5-Diamino-1,2,4-triazoleHCID 18462Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)-

Product 1

HCID 27641257-(2-thienyl)[1,2,4]triazolo[1,5-a]pyrimidin-2-amineYield 66.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

The obtained 3-dimethylamino-1-thiophen-2-ylpropenone (10.78 g) was dissolved in toluene (160 ml). Thereafter, 3,5-diamino-1,2,4-triazole (14.15 g) was added to the solution, and the obtained mixture was stirred at 100° C. After 10-camphorsulfonic acid (13.82 g) was added thereto, the mixture was heated to reflux for 1.5 hours. The reaction solution was cooled to a room temperature, and the supernatant was then eliminated (decant). The residue was washed by successive suspension in an aqueous 5% sodium carbonate-10% ethanol solution, a 10% ethanol solution, ethanol, and methylene chloride. The resultant was then dried under a reduced pressure to obtain the captioned compound (8.55 g).

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 1.5 hours
  3. temperatureThe reaction solution was cooled to a room temperature
  4. custom(decant)
  5. washThe residue was washed by successive suspension in an aqueous 5% sodium carbonate-10% ethanol solution
  6. customThe resultant was then dried under a reduced pressure

Sources & evidence

ORD record
ord-856967322d0e4b349dd1e4141bb0f781
Source dataset
uspto-grants-2009_10
Patent number
US07598244B2

Reaction notes

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