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

HRID 2305

Reaction equation

HRID 2305 reaction equation
Cl[C:2]1[N:7]=[CH:6][N:5]=[C:4]([NH2:8])[C:3]=1[C:9]1[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][CH:10]=1.[H-].[Na+].[Cl-].[NH4+].[CH2:20]([OH:23])[CH2:21][OH:22]>>[NH2:8][C:4]1[N:5]=[CH:6][N:7]=[C:2]([O:22][CH2:21][CH2:20][OH:23])[C:3]=1[C:9]1[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][CH:10]=1

Participants

5

Reactant 4

HCID 174Ethylene GlycolHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 189311004-Amino-6-chloro-5-(4-methylphenyl)pyrimidine

Product 1

HCID 111182972-{6-Amino-5-(4-methylphenyl)-pyrimidin-4-yloxy}ethanol

Procedure

A mixture of 6-chloro-5-(4-methylphenyl)pyrimidin-4-amine (500 mg), ethylene glycol (10 ml) and sodium hydride (60% dispersion-type, 0.46 g) is reacted at 70° C. for two hours, and reacted at 90° C. for five hours. The mixture is treated with saturated aqueous ammonium chloride solution, and extracted with ethyl acetate. The ethyl acetate layer is washed, dried, and evaporated to remove the solvent. The residue is crystallized from hexane/ethyl acetate to give 2-{6-amino-5-(4-methylphenyl)pyrimidin-4-yloxy}-ethanol (422 mg).

Workup

  1. customis reacted at 70° C. for two hours
  2. customreacted at 90° C. for five hours
  3. extractionextracted with ethyl acetate
  4. washThe ethyl acetate layer is washed
  5. customdried
  6. customevaporated
  7. customto remove the solvent
  8. customThe residue is crystallized from hexane/ethyl acetate

Sources & evidence

ORD record
ord-c45d1e41cd734870bba0fc8cf09b8c4c
Source dataset
uspto-grants-1998_03
Patent number
US05728706

Linked notes

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