4,6-Dichloro-5-(4-methylphenyl)pyrimidine → 4-Amino-6-chloro-5-(4-methylphenyl)pyrimidine

HRID 2304

Reaction equation

HRID 2304 reaction equation
[Cl: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.[NH3:16].C(O)C>CCOCC>[Cl:1][C:2]1[N:3]=[CH:4][N:5]=[C:6]([NH2:16])[C:7]=1[C:8]1[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=1

Participants

4

Reactant 2

HCID 219795544,6-Dichloro-5-(4-methylphenyl)pyrimidineHCID 22020343Ethanol, reaction products with ammonia, distn. residues

Product 1

HCID 189311004-Amino-6-chloro-5-(4-methylphenyl)pyrimidine

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of 4,6-dichloro-5-(4-methylphenyl)pyrimidine (4.14 g) in ether (20 ml) is added 27% ammonia-ethanol solution (30 ml), and the reaction mixture is reacted at room temperature in a sealed tube for three days. The mixture is concentrated under reduced pressure, and the residue is purified by silica gel column chromatography (solvent; hexane/ethyl acetate=(10:1)~ethyl acetate) to give 6-chloro-5-(4-methylphenyl)pyrimidin-4-amine (1.89 g).

Workup

  1. customthe reaction mixture is reacted at room temperature in a sealed tube for three days
  2. concentrationThe mixture is concentrated under reduced pressure
  3. customthe residue is purified by silica gel column chromatography (solvent; hexane/ethyl acetate=(10:1)~ethyl acetate)

Sources & evidence

ORD record
ord-bd67cbfc2bdf4149825d464041c6164c
Source dataset
uspto-grants-1998_03
Patent number
US05728706

Linked notes

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