p-Toluenesulfonic acid → HCID 15486863, compound

HRID 1384065Notes

Reaction equation

HRID 1384065 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:28]([CH3:31])([CH3:30])O)[CH:5]=[C:6]([O:26][CH3:27])[C:7]=1[O:8][C:9]1[C:10]2[N:18]=[N:17][N:16]([CH:19]([CH2:23][CH2:24][CH3:25])[CH2:20][CH2:21][CH3:22])[C:11]=2[N:12]=[C:13]([CH3:15])[N:14]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1C=CC=CC=1>[Br:1][C:2]1[CH:3]=[C:4]([C:28]([CH3:31])=[CH2:30])[CH:5]=[C:6]([O:26][CH3:27])[C:7]=1[O:8][C:9]1[C:10]2[N:18]=[N:17][N:16]([CH:19]([CH2:20][CH2:21][CH3:22])[CH2:23][CH2:24][CH3:25])[C:11]=2[N:12]=[C:13]([CH3:15])[N:14]=1

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 9891821HCID 9891821, compound

Product 1

HCID 15486863HCID 15486863, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a solution of 3-bromo-5-methoxy-α,α-dimethyl-4-[(5-methyl-3-(1-propylbutyl)-3H-1,2,3-triazolo[4,5-d]pyrimidin-7-yl)-oxy]benzenemethanol (0.59 g) in 35 mL of benzene, a small quantity of p-toluene sulfonic acid was added. The solution was refluxed under azeotropic conditions for 1.5 hours. Once cooled to room temperature, the solution was washed with saturated NaHCO3 followed by water. The organic phase was dried over MgSO4 and the solvent was removed under reduced pressure. The residue was chromatographed silica gel using a mixture of 1:1 ethyl acetate and hexane to yield the title compound as a colorless solid, mp 110-115° C.

Workup

  1. temperatureThe solution was refluxed under azeotropic conditions for 1.5 hours
  2. washthe solution was washed with saturated NaHCO3
  3. dry with materialThe organic phase was dried over MgSO4
  4. customthe solvent was removed under reduced pressure
  5. customThe residue was chromatographed silica gel using
  6. additiona mixture of 1:1 ethyl acetate and hexane

Sources & evidence

ORD record
ord-b615ae62939446a49738ccaecc417557
Source dataset
uspto-grants-2001_07
Patent number
US06258809B1

Reaction notes

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