Ethanol → 7-Amino-5-ethoxy-2-(2-furyl)[1,2,4]triazolo[1,5-a][1,3,5]triazine

HRID 326554Notes

Reaction equation

HRID 326554 reaction equation
[NH2:1][C:2]1[N:7]2[N:8]=[C:9]([C:11]3[O:12][CH:13]=[CH:14][CH:15]=3)[N:10]=[C:6]2[N:5]=[C:4](S(C)(=O)=O)[N:3]=1.C1CCN2C(=NCCC2)CC1.[CH2:31]([OH:33])[CH3:32]>>[NH2:1][C:2]1[N:7]2[N:8]=[C:9]([C:11]3[O:12][CH:13]=[CH:14][CH:15]=3)[N:10]=[C:6]2[N:5]=[C:4]([O:33][CH2:31][CH3:32])[N:3]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 99708822-(Furan-2-yl)-5-(methylsulfonyl)-[1,2,4]triazolo[1,5-a][1,3,5]triazin-7-amine

Product 1

HCID 157299517-Amino-5-ethoxy-2-(2-furyl)[1,2,4]triazolo[1,5-a][1,3,5]triazine

Procedure

A solution of 7-amino-2-(2-furyl)-5-methylsulphonyl-[1,2,4]triazolo[1,5-a][1,3,5]triazine (1.6 g) in ethanol (40 ml) containing DBU (1.0 ml) was heated under reflux until no starting material remained by TLC analysis. The solvent was removed by evaporation and the residue purified by chromatography on silica using 5-10% v/v ethyl acetate in dichloromethane as eluant, followed by crystallisation from ethanol to give 7-amino-5-ethoxy-2-(2-furyl)-[1,2,4]triazolo[1,5-a][1,3,5]triazine as hygroscopic crystals, m.p. 211°-213° C.; microanalysis, found: C, 48.7; H, 4.5; N, 31.4; H2O, 1.2%; C10H10N6O2.0.33C2H5OH. 0.165H2O requires: C, 48.4; H, 4.7; N, 31.8; H2O, 1.1%; NMR: 1.05(t, 1H, CH3CH2OH), 1.35(t, 3H, CH3CH2), 3.4(q, CH3CH2OH), 4.3(q, 2H, CH3CH2O--), 6.7(dd, 1H, furyl-4H), 7.1(d, 1H, furyl-3H), 7.9(d, 1H, furyl-5H), 8.5-9.0(d, 2H, NH2); m/e 246 (M+).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux until no starting material
  3. customThe solvent was removed by evaporation
  4. customthe residue purified by chromatography on silica using 5-10% v/v ethyl acetate in dichloromethane as eluant
  5. customfollowed by crystallisation from ethanol

Sources & evidence

ORD record
ord-2c71772dde89487c8ff72d3230f334c2
Source dataset
uspto-grants-1993_12
Patent number
US05270311

Reaction notes

Loading…