HCID 23356633, compound → HCID 23356625, compound

HRID 233576Notes

Reaction equation

HRID 233576 reaction equation
Cl[C:2]1[C:7]([C:8]2[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][CH:9]=2)=[C:6]([NH:16][CH:17]2[CH2:21][CH2:20][CH2:19][CH2:18]2)[N:5]2[N:22]=[CH:23][N:24]=[C:4]2[N:3]=1>CO.[OH-].[Na+].[Pd]>[CH3:15][O:14][C:11]1[CH:12]=[CH:13][C:8]([C:7]2[CH:2]=[N:3][C:4]3[N:5]([N:22]=[CH:23][N:24]=3)[C:6]=2[NH:16][CH:17]2[CH2:21][CH2:20][CH2:19][CH2:18]2)=[CH:9][CH:10]=1

Participants

5

Reactant 1

HCID 23356633HCID 23356633, compound

Product 1

HCID 23356625HCID 23356625, compoundYield 57%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

5-Chloro-6-(4-methoxyphenyl)-7-cyclopentylamino1,2,4-triazolo[1,5-a]pyrimidine (5.1 g, 14.8 mmol), prepared by a method analogous to Example 1, was dissolved in a mixture of methanol (100 ml) and aqueous sodium hydroxide (1N, 15 ml), palladium (0.5 g; on charcoal, 5% E 10N) was added and the reaction mixture stirred for 3 hours under hydrogen (5 bar). The catalyst was removed by filtration and the filtrate evaporated in vacuo. Column chromatography of the residue on a silica gel column (3.5×15 cm) using 4:1 ethyl acetate: petroleum ether as eluant and evaporation of the solvent in vacuo gave 2.6 g 6-(4-methoxyphenyl)-7-cyclopentylamino-1,2,4-triazolo-[1,5-a]pyrimidine as colourless crystals, m.pt. 127° C. Yield: 57% of theoretical 1H-NMR: δ=1.35-1.75 (2 m,8H); 3.88 (s,3H); 6.16 (d,1H); 7.00 (dd,2H); 7.34 (m,2H); 8.32 (s,1H); 8.34 (s,1H) ppm

Workup

  1. additionwas added
  2. customThe catalyst was removed by filtration
  3. customthe filtrate evaporated in vacuo
  4. custompetroleum ether as eluant and evaporation of the solvent in vacuo

Sources & evidence

ORD record
ord-421154f5e72d48fbb7b520ecce94f333
Source dataset
uspto-grants-1997_01
Patent number
US05593996

Reaction notes

Loading…