2,4-Dichloropyrimidine → (2-Chloro-pyrimidin-4-yl)-(3-methoxy-2-methyl-phenyl)-amine

HRID 491220Notes

Reaction equation

HRID 491220 reaction equation
[CH3:1][O:2][C:3]1[C:4]([CH3:10])=[C:5]([NH2:9])[CH:6]=[CH:7][CH:8]=1.[Cl:11][C:12]1[N:17]=[C:16](Cl)[CH:15]=[CH:14][N:13]=1>C(O)C.C(Cl)Cl>[Cl:11][C:12]1[N:17]=[C:16]([NH:9][C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[C:4]=2[CH3:10])[CH:15]=[CH:14][N:13]=1

Participants

5

Reactant 2

HCID 775312,4-DichloropyrimidineHCID 118048223-Methoxy-2-methylaniline

Product 1

HCID 57516499(2-Chloro-pyrimidin-4-yl)-(3-methoxy-2-methyl-phenyl)-amineYield 7%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 3-methoxy-2-methyl-phenylamine (0.68 g, 5 mmol) and 2,4-dichloro-pyrimidine (0.74 g, 5 mmol) were suspended in ethyl alcohol (10 mL) and stirred at room temperature for 20 h. The reaction mixture was diluted with DCM (50 mL), filtered and concentrated in vacuo. The residue was purified by silica gel column chromatography to afford the title compound (0.085 g, 7%) as yellow solids.

Workup

  1. filtrationfiltered
  2. concentrationconcentrated in vacuo
  3. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-95bf3d20ceb14b9d8dc487bb24a99ecb
Source dataset
uspto-grants-2009_05
Patent number
US07528143B2

Reaction notes

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