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

HRID 1599031Notes

Reaction equation

HRID 1599031 reaction equation
[NH2:1][C:2]1[C:7]([C:8]2[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=2)=[C:6](Cl)[N:5]=[CH:4][N:3]=1.[H-].[Na+].[Cl-].[NH4+].[CH2:20]([OH:23])[CH2:21][OH:22]>>[NH2:1][C:2]1[N:3]=[CH:4][N:5]=[C:6]([O:22][CH2:21][CH2:20][OH:23])[C:7]=1[C:8]1[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=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 4-amino-6-chloro-5-(4-methylphenyl)pyrimidine (500 mg), ethylene glycol (10 ml) and sodium hydride (60% dispersion, 0.46 g) is reacted at 70° C. for two hours, and then reacted at 90° C. for five hours. The reaction mixture is treated with a saturated ammonium chloride solution, and extracted with ethyl acetate. The ethyl acetate layer is washed, dried, and evaporated under reduced pressure 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 under reduced pressure
  7. customto remove the solvent
  8. customThe residue is crystallized from hexane-ethyl acetate

Sources & evidence

ORD record
ord-b80b32b3886d4867b4b284f46d0973e2
Source dataset
uspto-grants-1998_04
Patent number
US05739333

Reaction notes

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