Ethylene Glycol → 2-{6-Chloro-5-(4-methylphenyl)pyrimidin-4-yloxy}ethanol

HRID 1599029Notes

Reaction equation

HRID 1599029 reaction equation
O1CCCC1.[CH2:6]([OH:9])[CH2:7][OH:8].[H-].[Na+].[Cl:12][C:13]1[C:18]([C:19]2[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=2)=[C:17](Cl)[N:16]=[CH:15][N:14]=1>C(O)(=O)C>[Cl:12][C:13]1[N:14]=[CH:15][N:16]=[C:17]([O:8][CH2:7][CH2:6][OH:9])[C:18]=1[C:19]1[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=1

Participants

6

Reactant 4

HCID 174Ethylene GlycolHCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 219795544,6-Dichloro-5-(4-methylphenyl)pyrimidine

Product 1

HCID 111189672-{6-Chloro-5-(4-methylphenyl)pyrimidin-4-yloxy}ethanol

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a mixture of tetrahydrofuran (400 ml) and ethylene glycol (60 ml) is added with stirring sodium hydride (60% dispersion, 3.38 g) under ice-cooling, and thereto is added 4,6-dichloro-5-(4-methylphenyl)pyrimidine (20.0 g). The mixture is stirred under ice-cooling for 30 minutes, and then stirred at room temperature for two hours. The mixture is weakly acidified with acetic acid, and concentrated under reduced pressure. The residue is dissolved in ethyl acetate, and washed, dried, and concentrated to dryness under reduced pressure. The residue is crystallized from hexane to give 2-{6-chloro-5-(4-methylphenyl)pyrimidin-4-yloxy}ethanol (21.85 g).

Workup

  1. temperaturecooling
  2. temperaturecooling for 30 minutes
  3. stirringstirred at room temperature for two hours
  4. concentrationconcentrated under reduced pressure
  5. dissolutionThe residue is dissolved in ethyl acetate
  6. washwashed
  7. customdried
  8. concentrationconcentrated to dryness under reduced pressure
  9. customThe residue is crystallized from hexane

Sources & evidence

ORD record
ord-443b6a410d644885b063dcd42d3ef063
Source dataset
uspto-grants-1998_04
Patent number
US05739333

Reaction notes

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