N,N'-Dimethylethylenediamine → 2-furan-2-yl-N5-methyl-N5-(2-methylamino-ethyl)-[1,2,4]triazolo[1,5-a][1,3,5]triazine-5,7-diamine

HRID 1181306Notes

Reaction equation

HRID 1181306 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[N:19]=[C:9]2[N:10]=[C:11](S(C)(=O)=O)[N:12]=[C:13]([NH2:14])[N:8]2[N:7]=1.[CH3:20][NH:21][CH2:22][CH2:23][NH:24][CH3:25]>CC#N>[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[N:19]=[C:9]2[N:10]=[C:11]([N:21]([CH3:20])[CH2:22][CH2:23][NH:24][CH3:25])[N:12]=[C:13]([NH2:14])[N:8]2[N:7]=1

Participants

4

Reactant 2

HCID 8070N,N'-DimethylethylenediamineHCID 99708822-(Furan-2-yl)-5-(methylsulfonyl)-[1,2,4]triazolo[1,5-a][1,3,5]triazin-7-amine

Product 1

HCID 694334172-furan-2-yl-N5-methyl-N5-(2-methylamino-ethyl)-[1,2,4]triazolo[1,5-a][1,3,5]triazine-5,7-diamine

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

2-Furan-2-yl-5-methanesulfonyl-[1,2,4]triazolo[1,5-a][1,3,5]triazin-7-ylamine (18 mmol; see Example 1(a) above) was suspended in 50 mL of CH3CN along with 5 eq. of N,N′-dimethyl-ethane-1,2-diamine. The reaction mixture was stirred under reflux for 2 hours. It was then cooled to room temperature and concentrated under reduced pressure. The residue was taken up in CH2Cl2 and washed with H2O, brine, dried with Na2SO4, and concentrated under reduced pressure. The resulting crude product was purified by chromatography (95% CH2Cl2, 4% MeOH, 1% Et3N) to afford 2-furan-2-yl-N5-methyl-N5-(2-methylamino-ethyl)-[1,2,4]triazolo[1,5-a][1,3,5]triazine-5,7-diamine.

Workup

  1. temperatureunder reflux for 2 hours
  2. concentrationconcentrated under reduced pressure
  3. washwashed with H2O, brine
  4. dry with materialdried with Na2SO4
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting crude product was purified by chromatography (95% CH2Cl2, 4% MeOH, 1% Et3N)

Sources & evidence

ORD record
ord-b10032e8796948e284a09b7a3fddc766
Source dataset
uspto-grants-2007_10
Patent number
US07285550B2

Reaction notes

Loading…