3-Pentanol → 4-(1-Ethylpropoxy)-2,5-dimethyl-6-(2,4,6-trimethylphenoxy)pyrimidine

HRID 967952Notes

Reaction equation

HRID 967952 reaction equation
[CH3:1][CH2:2][CH:3]([OH:6])[CH2:4][CH3:5].[H-].[Na+].Cl[C:10]1[C:15]([CH3:16])=[C:14]([O:17][C:18]2[C:23]([CH3:24])=[CH:22][C:21]([CH3:25])=[CH:20][C:19]=2[CH3:26])[N:13]=[C:12]([CH3:27])[N:11]=1>CS(C)=O>[CH2:2]([CH:3]([O:6][C:10]1[C:15]([CH3:16])=[C:14]([O:17][C:18]2[C:19]([CH3:26])=[CH:20][C:21]([CH3:25])=[CH:22][C:23]=2[CH3:24])[N:13]=[C:12]([CH3:27])[N:11]=1)[CH2:4][CH3:5])[CH3:1]

Participants

5

Reactant 3

HCID 114283-PentanolHCID 24758Sodium hydrideHCID 219120504-Chloro-2,5-dimethyl-6-(2,4,6-trimethylphenoxy)-pyrimidine

Product 1

HCID 99055074-(1-Ethylpropoxy)-2,5-dimethyl-6-(2,4,6-trimethylphenoxy)pyrimidine

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A mixture of 3-pentanol (0.3 ml) and sodium hydride (60% in oil, 32 mg, 0.81 mmol) in DMSO was stirred at room temperature for 5 minutes. 4-Chloro-2,5-dimethyl-6-(2,4,6-trimethylphenyoxy)-pyrimidine (150 mg, 0.54 mmol) was added and the resulting mixture was heated at 150° C. for 5 hours. The mixture was quenched with water and extracted with ethyl acetate. The organic layer was separated, dried and concentrated to give a beige solid. The solid was purified through silica gel column chromatography using 20% chloroform in hexane as eluent to give the title compound as white crystals, mp 93.5-95.5° C. 1H NMR (CDCl3) δ 6.85 (s, 2H), 5.11 (t, 1H), 2.27 (s, 3H), 2.26 (s, 3H), 2.11 (s, 3H), 2.03 (s, 6H), 1.68 (p, 4H), 0.92 (t, 6H) ppm.

Workup

  1. temperaturethe resulting mixture was heated at 150° C. for 5 hours
  2. customThe mixture was quenched with water
  3. extractionextracted with ethyl acetate
  4. customThe organic layer was separated
  5. customdried
  6. concentrationconcentrated
  7. customto give a beige solid
  8. customThe solid was purified through silica gel column chromatography

Sources & evidence

ORD record
ord-3db83b8d0a71428dabe165ff7eed1ba6
Source dataset
uspto-grants-2005_10
Patent number
US06956047B1

Reaction notes

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