4-Chlorophenol → 7-[1-(4-Chlorophenoxy)ethyl]-[1,2,4]triazolo[1,5-a]pyrimidine

HRID 1290826Notes

Reaction equation

HRID 1290826 reaction equation
[N:1]1[N:5]2[C:6]([CH:10]([OH:12])[CH3:11])=[CH:7][CH:8]=[N:9][C:4]2=[N:3][CH:2]=1.CCOC(/N=N/C(OCC)=O)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Cl:44][C:45]1[CH:50]=[CH:49][C:48](O)=[CH:47][CH:46]=1>O1CCCC1>[Cl:44][C:45]1[CH:50]=[CH:49][C:48]([O:12][CH:10]([C:6]2[N:5]3[N:1]=[CH:2][N:3]=[C:4]3[N:9]=[CH:8][CH:7]=2)[CH3:11])=[CH:47][CH:46]=1

Participants

6

Reactant 4

HCID 46844-ChlorophenolHCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 109208511-(1,2,4-Triazolo[1,5-a]pyrimidin-7-yl)ethanol

Product 1

HCID 38017397-[1-(4-Chlorophenoxy)ethyl]-[1,2,4]triazolo[1,5-a]pyrimidine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of (-)-1-(1,2,4-triazolo[1,5-a]pyrimidin-7-yl)ethanol (0.27 g), diethylazodicarboxylate (0.44 g), triphenylphosphine (0.68 g) and 4-chlorophenol (0.22 g) in dry tetrahydrofuran (20 ml) was stood overnight at ambient temperature until the reaction was complete. The solvent was removed under reduced pressure and the residue dissolved in ethyl acetate (100 ml). The solution was washed with 1M sodium hydroxide (40 ml) followed by brine (20 ml), and the solvent was evaporated. The residue was purified by flash chromatography on silica gel using as eluent a mixture of triethylamine and ethyl acetate (in the ratio 1:100 respectively) to give (-)-7-[1-(4-chlorophenoxy)ethyl]-1,2,4-triazolo[1,5-a]pyrimidine. Yield 0.26 g.

Workup

  1. customThe solvent was removed under reduced pressure
  2. dissolutionthe residue dissolved in ethyl acetate (100 ml)
  3. washThe solution was washed with 1M sodium hydroxide (40 ml)
  4. customthe solvent was evaporated
  5. customThe residue was purified by flash chromatography on silica gel using as eluent
  6. additiona mixture of triethylamine and ethyl acetate (in the ratio 1:100 respectively)

Sources & evidence

ORD record
ord-b1b24b9f076743c5aecfcdf0ac8f6e81
Source dataset
uspto-grants-1998_05
Patent number
US05753665

Reaction notes

Loading…