dimethyl-1H-1,2,4-triazol-3-amine → 4-((1,5-dimethyl-1H-1,2,4-triazol-3-yl)amino)-2-(methylthio)imidazo[2,1-f][1,2,4]triazine-7-carbonitrile

HRID 921752Notes

Reaction equation

HRID 921752 reaction equation
[CH3:1][N:2]1[C:6]([CH3:7])=[N:5][C:4]([NH2:8])=[N:3]1.CC(C)([O-])C.[Na+].[CH3:15][S:16][C:17]1[N:22]=[C:21](SC)[C:20]2=[N:25][CH:26]=[C:27]([C:28]#[N:29])[N:19]2[N:18]=1>C1COCC1>[CH3:1][N:2]1[C:6]([CH3:7])=[N:5][C:4]([NH:8][C:21]2[C:20]3=[N:25][CH:26]=[C:27]([C:28]#[N:29])[N:19]3[N:18]=[C:17]([S:16][CH3:15])[N:22]=2)=[N:3]1

Participants

5

Reactant 3

HCID 307976dimethyl-1H-1,2,4-triazol-3-amineHCID 23676156Sodium t-butoxideHCID 710653752,4-Bis(methylthio)imidazo[2,1-f][1,2,4]triazine-7-carbonitrile

Product 1

HCID 867086354-((1,5-dimethyl-1H-1,2,4-triazol-3-yl)amino)-2-(methylthio)imidazo[2,1-f][1,2,4]triazine-7-carbonitrile

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

1,5-dimethyl-1H-1,2,4-triazol-3-amine (170 mg, 1.517 nmmol) was taken up in 6 ml of anhydrous THF and cooled to 0° C. Sodium tert-butoxide (243 mg, 2.53 mmol) was added and the reaction was stirred at 0° C. for 5 min. Next, a solution of 2,4-bis(methylthio)imidazo[2,1-f][1,2,4]triazine-7-carbonitrile (Intermediate (300 mg, 1.264 mmol) in 8 ml of THF was added, and the reaction was brought to rt. The reaction was stirred at room temperature for 1 h. The solvent was removed in vacuo and the material was dissolved in EtOAc. The organic layer was washed once with water, and the aqueous layer was re-extracted with EtOAc. The organic layers were combined, washed with brine, dried over Na2SO4, filtered and concentrated to give 4-((1,5-dimethyl-1H-1,2,4-triazol-3-yl)amino)-2-(methylthio)imidazo[2,1-f][1,2,4]triazine-7-carbonitrile (157 mg) as a yellow solid. The crude material was taken onto the next step without further purification.

Workup

  1. customwas brought to rt
  2. stirringThe reaction was stirred at room temperature for 1 h
  3. customThe solvent was removed in vacuo
  4. dissolutionthe material was dissolved in EtOAc
  5. washThe organic layer was washed once with water
  6. extractionthe aqueous layer was re-extracted with EtOAc
  7. washwashed with brine
  8. dry with materialdried over Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-8e06ff805e5b4206a827fba988ec0bac
Source dataset
uspto-grants-2016_03
Patent number
US09273057B2

Reaction notes

Loading…