Acetic Acid → HCID 15730078, compound

HRID 326555Notes

Reaction equation

HRID 326555 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]([O:16][C:17]2[CH:22]=[CH:21][C:20]([O:23]CC3C=CC=CC=3)=[CH:19][CH:18]=2)[N:3]=1.C(O)(=O)C.[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]([O:16][C:17]2[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][CH:18]=2)[N:3]=1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 15729954HCID 15729954, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 15730078HCID 15730078, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 7-amino-5-(4-benzyloxyphenoxy)-2-(2-furyl)-[1,2,4]triazolo[1,5-a][1,3,5]triazine (1.0 g) in methanol (400 ml) containing palladium-on-carbon catalyst (10% w/w, 200 mg) and acetic acid (20 ml) was treated with hydrogen gas at atmospheric pressure. The reaction was monitored by tlc analysis (system as Example 1) and once no further starting material was detected, the catalyst was removed by filtration. Solvent was evaporated from the filtrate. The solid residue obtained was crystallised from ethanol to give 7-amino-2-(2-furyl)-5-(4-hydroxyphenoxy)-[1,2,4]triazolo[1,5-a][1,3,5]triazine as colourless hygroscopic crystals, m.p. 292°-294° C.; microanalysis, found: C, 53.5; H, 3.6; N, 26.4; H2O, 2.1%; C14H10N6O3 0.33H2O requires: C, 53.2; H, 3.4; N, 26.6; H, 3.6; N, 26.4; H2O, 2.1 %; NMR: 6.7(dd, 1H, furyl-4H), 6.8(d, 2H, phenyl), 7.0(d, 2H, phenyl), 7.1(d, 1H, furyl-3H), 7.9(d, 1H, furyl-5H), 8.7-9.1(d, 2H, NH2), 9.4(br s, 1H, OH; m/e 310 (M+).

Workup

  1. customthe catalyst was removed by filtration
  2. customSolvent was evaporated from the filtrate
  3. customThe solid residue obtained
  4. customwas crystallised from ethanol

Sources & evidence

ORD record
ord-073dc794c8d84fd9b3ccc6d490102b1f
Source dataset
uspto-grants-1993_12
Patent number
US05270311

Reaction notes

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