Ammonia → 4-Amino-6-chloro-5-(4-methylphenyl)pyrimidine

HRID 1599030Notes

Reaction equation

HRID 1599030 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]>CCOCC.CO>[NH2:16][C:6]1[C:7]([C:8]2[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=2)=[C:2]([Cl:1])[N:3]=[CH:4][N:5]=1

Participants

5

Reactant 2

HCID 222AmmoniaHCID 219795544,6-Dichloro-5-(4-methylphenyl)pyrimidine

Product 1

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

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 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 in methanol solution (30 ml), and the mixture is reacted at room temperature for three days in a sealed tube. The mixture is evaporated under reduced pressure to remove the solvent, and the residue is purified by silica gel column chromatography (solvent; hexane:ethyl acetate=10:1~ethyl acetate only) to give 4-amino-6-chloro-5-(4-methyl-phenyl)pyrimidine (1.89 g).

Workup

  1. customthe mixture is reacted at room temperature for three days in a sealed tube
  2. customThe mixture is evaporated under reduced pressure
  3. customto remove the solvent
  4. customthe residue is purified by silica gel column chromatography (solvent

Sources & evidence

ORD record
ord-6995eb8925604a8aafb9b16d37b1c2a4
Source dataset
uspto-grants-1998_04
Patent number
US05739333

Reaction notes

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