7-Amino-5-[(4-benzyloxyphenyl)methyl]amino-2-(2-furyl)-[1,2,4]triazolo[1,5-a][1,3,5]triazine → HCID 16128681, compound

HRID 5821Notes

Reaction equation

HRID 5821 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][C:18]2[CH:23]=[CH:22][C:21]([O:24]CC3C=CC=CC=3)=[CH:20][CH:19]=2)[N:3]=1>C(OCC)(=O)C.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][C:18]2[CH:19]=[CH:20][C:21]([OH:24])=[CH:22][CH:23]=2)[N:3]=1

Participants

5

Reactant 1

HCID 197943327-Amino-5-[(4-benzyloxyphenyl)methyl]amino-2-(2-furyl)-[1,2,4]triazolo[1,5-a][1,3,5]triazine

Product 1

HCID 16128681HCID 16128681, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 7-amino-5-[(4-benzyloxyphenyl)methyl]amino-2-(2-furyl)-[1,2,4]triazolo[1,5-a][1,3,5]triazine (2.37 g) in ethyl acetate (150 ml) and methanol (150 ml) was treated with 10% palladium on carbon (3.0 g) and hydrogenated at atmospheric pressure for 2.5 hours. The catalyst was filtered through diatomaceous earth and the liquors evaporated. The residue was purified by chromatography on silica (100 g) eluting with dichloromethane containing methanol 3-30% v/v, and gave 7-amino-2-(2-furyl)-5-[(4-hydroxyphenyl)methyl]amino-[1,2,4]-triazolo[1,5-a][1,3,5]triazine, m.p. 268-270; NMR: 4.39 (d, 2H, CH2N), 6.64 (d of d, 1H, furyl-4H), 6.68 and 7.13 (A2B2 pattern, 4H, phenyl-H), 7.03 (d, 1H, furyl-3H), 7.8 (t, 1H, NH), 7.84 (d, 1H, furyl-5H), 8.13 (br s, 2H, NH2) and 9.19 (s, 1H, OH); m/e 324 (M+H)+.

Workup

  1. filtrationThe catalyst was filtered through diatomaceous earth
  2. customthe liquors evaporated
  3. customThe residue was purified by chromatography on silica (100 g)
  4. washeluting with dichloromethane
  5. additioncontaining methanol 3-30% v/v

Sources & evidence

ORD record
ord-77c7e60be0494129bd4ab11177e4baf3
Source dataset
uspto-grants-1993_09
Patent number
US05246932

Reaction notes

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