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

HRID 1290821Notes

Reaction equation

HRID 1290821 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 11776Triphenylphosphine2×HCID 5462977Diethyl azodicarboxylate2×HCID 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 (0.29 g), triphenylphosphine (0.44 g) and 4-chlorophenol (0.22 g) in dry tetrahydrofuran (40 ml) was stirred at ambient temperature for 2 days. Further diethylazodicarboxylate (0.15 g) and triphenylphosphine (0.22 g) was added to the solution, which was stirred overnight until the reaction was complete. The solvent was removed under reduced pressure and the residue was dissolved in ethyl acetate (100 ml). This 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 0.33 g.

Workup

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

Sources & evidence

ORD record
ord-5e94a61c002946a58951d11732e983fb
Source dataset
uspto-grants-1998_05
Patent number
US05753665

Reaction notes

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