HCID 15730112, compound → HCID 15730117, compound

HRID 5822Notes

Reaction equation

HRID 5822 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]([NH:16][CH2:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[O:25]CC2C=CC=CC=2)[N:3]=1.[H][H]>CO.[Pd]>[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]([NH:16][CH2:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[OH:25])[N:3]=1

Participants

5

Reactant 2

HCID 15730112HCID 15730112, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 15730117HCID 15730117, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of the product of step (1) (0.9g) in methanol (150 ml) was hydrogenated at room-temperature and pressure using 10% palladium on carbon (0.9 g) catalyst. After the uptake of hydrogen was complete, the catalyst was filtered off and the solvent evaporated. The residue was crystallised from ethanol, and gave 7-amino-2-(2-furyl)-5-[2-(hydroxyphenyl)ethyl]amino-[1,2,4]triazolo[1,5-a][1,3,5]triazine, m.p. 260°-263° C. microanalysis, found: C, 57.2; H, 4.8; N, 28.6%; C16H15N7O2 (0.15) C2H5OH requires: C, 57.0; H, 4.7; N, 28.5%; NMR: 2.81 (t, 2H, phenyl-H), 3.49 (m, 2H, CH2N); 6.71 (d of d, 1H, furyl-4H), 7.03 (d, 1H, furyl-3H), 6.7-7.15 (complex, 4H, phenyl-H); 7.85 (m, 1H, NH); 7.84 (s, 1H, furyl-5H); 8.09 (br s, 2H, NH2) and 9.31 (s, 1H, OH); m/e 338 (M+H)+.

Workup

  1. filtrationthe catalyst was filtered off
  2. customthe solvent evaporated
  3. customThe residue was crystallised from ethanol

Sources & evidence

ORD record
ord-b75301676eb1424c9eacfe2ac252c8f5
Source dataset
uspto-grants-1993_09
Patent number
US05246932

Reaction notes

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