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

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

Reactant 4

HCID 174Ethylene Glycol

HCID 24758Sodium hydride

HCID 25517Ammonium Chloride

HCID 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).