2,4,6-Trimethylphenol → HCID 15486864, compound

HRID 1384067Notes

Reaction equation

HRID 1384067 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([CH3:9])[C:3]=1[OH:10].C[O-].[Na+].Cl[C:15]1[C:16]2[N:24]=[N:23][N:22]([CH:25]([CH2:28][CH3:29])[CH2:26][CH3:27])[C:17]=2[N:18]=[C:19]([CH3:21])[N:20]=1>C(#N)C>[CH2:26]([CH:25]([N:22]1[C:17]2[N:18]=[C:19]([CH3:21])[N:20]=[C:15]([O:10][C:3]3[C:4]([CH3:9])=[CH:5][C:6]([CH3:8])=[CH:7][C:2]=3[CH3:1])[C:16]=2[N:24]=[N:23]1)[CH2:28][CH3:29])[CH3:27]

Participants

5

Reactant 3

HCID 106982,4,6-TrimethylphenolHCID 10942334Sodium MethoxideHCID 21186063HCID 21186063, compound

Product 1

HCID 15486864HCID 15486864, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Conditions

Temperature
2.5 °C

Procedure

2,4,6-Trimethylphenol (0.114) was added to a solution of sodium methoxide (0.334 g) methanol (10 mL) and the resulting solution was evaporated to dryness under reduced pressure. The salt thus obtained was taken up in 10 mL of acetonitrile and added dropwise by to a cold solution (0-5° C.) of 7-chloro-3-(1-ethylpropyl)-5-methyl-3H-1,2,3-triazolo[4,5-d]pyrimidine in 35 mL of acetonitrile, such that the temperature did not rise above 5° C. The mixture was stirred at 0-5° C. for 3 hours. The solvent was then removed from the mixture under reduced pressure and the residue treated with water and extracted three times with methylene chloride. The combined extracts were dried over MgSO4 and stripped of the solvent under reduced pressure. The material was purified on silica gel using a solution of 1% methanol in methylene chloride to yield the title compound as a colorless powder, mp 92° C.

Workup

  1. customthe resulting solution was evaporated to dryness under reduced pressure
  2. customThe salt thus obtained
  3. customdid not rise above 5° C
  4. customThe solvent was then removed from the mixture under reduced pressure
  5. additionthe residue treated with water
  6. extractionextracted three times with methylene chloride
  7. dry with materialThe combined extracts were dried over MgSO4
  8. customThe material was purified on silica gel using a solution of 1% methanol in methylene chloride

Sources & evidence

ORD record
ord-1fb1779cd15744a58540966d2f03e36d
Source dataset
uspto-grants-2001_07
Patent number
US06258809B1

Reaction notes

Loading…