4,6-Dichloropyrimidine → HCID 21708388, compound

HRID 651421Notes

Reaction equation

HRID 651421 reaction equation
Cl[C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[CH:4][N:3]=1.[CH3:9][NH:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([C:17]([F:20])([F:19])[F:18])[CH:12]=1>C(OCC)(=O)C>[Cl:8][C:6]1[CH:7]=[C:2]([N:10]([CH3:9])[C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([C:17]([F:18])([F:19])[F:20])[CH:12]=2)[N:3]=[CH:4][N:5]=1

Participants

4

Reactant 2

HCID 709434,6-DichloropyrimidineHCID 2783214N-methyl-3-(trifluoromethyl)aniline

Product 1

HCID 21708388HCID 21708388, compoundYield 61.9%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
126 °C

Procedure

4,6-Dichloropyrimidine (1.55 g, 0.01 mol) and N-metyl-3-trifluoromethylaniline (2.0 g, 0.11 mol) are combined and heated to 126° C. under N2 for 1.5 hours. The resulting oil is taken up in ethyl acetate, is washed with 10% sodium carbonate and dried over sodium sulphate. The organic phase is concentrated under reduced pressure to yield a yellow oil which is purified by column chromatography to give 4-chloro-6-(N-methyl-3-trifluoromethylanilino)-pyrimidine (1.78 g) as a white solid.

Workup

  1. washis washed with 10% sodium carbonate
  2. dry with materialdried over sodium sulphate
  3. concentrationThe organic phase is concentrated under reduced pressure
  4. customto yield a yellow oil which
  5. customis purified by column chromatography

Sources & evidence

ORD record
ord-e93bc94aba7849c69058cb7834a3b6f3
Source dataset
uspto-grants-2001_08
Patent number
US06281219B1

Reaction notes

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