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

HRID 1737671Notes

Reaction equation

HRID 1737671 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) δ6.85 (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-fff6ea780bb54f4a8703dc258d1236e8
Source dataset
uspto-grants-1999_10
Patent number
US05962479

Reaction notes

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