Methanol → HCID 15730117, compound

HRID 326567Notes

Reaction equation

HRID 326567 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][C:22](OC)=[CH:21][CH:20]=2)[N:3]=1.[H][H].C[OH:30]>[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:20]=[CH:21][CH:22]=[CH:23][C:24]=2[OH:30])[N:3]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 15730111HCID 15730111, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 15730117HCID 15730117, compound

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

A solution of the product of Example 161 (0.9 g) 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 (brs, 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-3f34a74e0d214ceaa9de2b7845ceb0e3
Source dataset
uspto-grants-1993_12
Patent number
US05270311

Reaction notes

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