反应详情

7-amino-2-(2-furyl)-5-[2-(4-hydroxyphenyl)ethyl]amino[1,2,4]-triazolo[1,5-a][1,3,5]triazine (0.91 g) and 1,8-diazabicyclo[5,4,0]undec-7-ene (DBU, 0.37 ml) were added to a suspension of 7-amino-2-(2-furyl)-5-methylsulphonyl-[1,2,4]triazolo[1,5-a][1,3,5]triazine (0.82 g) in acetonitrile (50 ml) and the resulting mixture was heated under reflux for 17 hours, after which time thin layer chromatography (TLC) analysis on silica plates (eluent: methylene chloride-methanol 19:1 v/v) indicated that no methanesulphonyl starting material remained. The solvent was then evaporated and the residue was purified by column chromatography on silica (75 g) eluting with ethyl acetate-methylene chloride 7:3 v/v. A white solid was obtained, and this was crystallised from isopropanol to afford 7-amino-5-[4-(2-[7-amino-2-(2-furyl)-[1,2,4]triazolo[1,5-a][1,3,5]triazin-5-ylamino]ethyl)phenoxy]-2-(2-furyl)[ 1,2,4]triazolo[1,5-a][1,3,5]triazine, m.p. 285°-289° C.; microanalysis, found: C, 54.1; H, 4.4; N, 30.8%; C24H19N13O3 1.0(C3H7OH) requires: C, 54.2; H, 4.5; N, 30.5%; NMR: 2.92 (t, 2H, phenyl-CH2), 3.55 (q, 2H, CH2-N), 6.67 (m, 2H, 2 furyl-4H), 7.0 (d, 1H, furyl-3H), 7.11 (d, 1H, furyl-3'H), 7.16 and 7.35 (A2B2 pattern, 4H, phenyl-H), 7.5 (br t, 1H, NH rotamers), 7.85 (d, 1H, furyl-5H), 7.89 (d, 1H, furyl-5'H), 8.12 (br s, 2H, NH2) and 8.93 (d, 2H, NH2); m/e (M+H)+ 538.

1. temperaturethe resulting mixture was heated
2. temperatureunder reflux for 17 hours
3. customThe solvent was then evaporated
4. customthe residue was purified by column chromatography on silica (75 g)
5. washeluting with ethyl acetate-methylene chloride 7:3 v/v
6. customA white solid was obtained
7. customthis was crystallised from isopropanol