4,6-Dichloropyrimidine → 714962-04-6

HRID 1408485Notes

Reaction equation

HRID 1408485 reaction equation
Cl[C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[CH:4][N:3]=1.[F:9][C:10]([F:20])([F:19])[O:11][C:12]1[CH:18]=[CH:17][C:15]([NH2:16])=[CH:14][CH:13]=1.CCN(C(C)C)C(C)C>CCO>[Cl:8][C:6]1[N:5]=[CH:4][N:3]=[C:2]([NH:16][C:15]2[CH:17]=[CH:18][C:12]([O:11][C:10]([F:9])([F:19])[F:20])=[CH:13][CH:14]=2)[CH:7]=1

Participants

5

Reactant 3

HCID 709434,6-DichloropyrimidineHCID 81531DiisopropylethylamineHCID 6008484-(Trifluoromethoxy)aniline

Product 1

HCID 5311508714962-04-6Yield 84%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4,6-Dichloropyrimidine (250 mg, 3.3 mmol) and 4-trifluoromethoxy aniline (330.5 mg, 1.8 mmol) were dissolved in EtOH and DIEA (312.5 uL, 1.8 mmol) was added and the mixture was refluxed for 4 h. It was then cooled, concentrated and work-up with ethyl acetate. The organic layer was separated and dried (Na2SO4). Concentrated and purified by silica-gel column chromatography (Ethyl acetate/hexane). 400 mg (84% Yield). MS m/z 290.04 (M+1).

Workup

  1. temperaturethe mixture was refluxed for 4 h
  2. temperatureIt was then cooled
  3. concentrationconcentrated
  4. customThe organic layer was separated
  5. dry with materialdried (Na2SO4)
  6. concentrationConcentrated
  7. custompurified by silica-gel column chromatography (Ethyl acetate/hexane)

Sources & evidence

ORD record
ord-840fea30c50a47f787fc17ff2683f900
Source dataset
uspto-grants-2014_12
Patent number
US08921336B2

Reaction notes

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