4-Amino-3,5-dichlorobenzotrifluoride → 4-[[4-[2,6-Dichloro-4-(trifluoromethyl)anilino]pyrimidin-2-yl]amino]benzonitrile

HRID 1070951Notes

Reaction equation

HRID 1070951 reaction equation
FC(F)(F)S(O[C:7]1[CH:12]=[CH:11][N:10]=[C:9]([NH:13][C:14]2[CH:19]=[CH:18][C:17]([C:20]#[N:21])=[CH:16][CH:15]=2)[N:8]=1)(=O)=O.[Cl:24][C:25]1[CH:30]=[C:29]([C:31]([F:34])([F:33])[F:32])[CH:28]=[C:27]([Cl:35])[C:26]=1[NH2:36]>O1CCOCC1>[Cl:24][C:25]1[CH:30]=[C:29]([C:31]([F:34])([F:32])[F:33])[CH:28]=[C:27]([Cl:35])[C:26]=1[NH:36][C:7]1[CH:12]=[CH:11][N:10]=[C:9]([NH:13][C:14]2[CH:15]=[CH:16][C:17]([C:20]#[N:21])=[CH:18][CH:19]=2)[N:8]=1

Participants

4

Reactant 2

HCID 1410944-Amino-3,5-dichlorobenzotrifluorideHCID 223984512-[(4-Cyanophenyl)amino]4-pyrimidinyl trifluoromethanesulfonate

Product 1

HCID 4887744-[[4-[2,6-Dichloro-4-(trifluoromethyl)anilino]pyrimidin-2-yl]amino]benzonitrileYield 9.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
170 °C

Procedure

2-[(4-cyanophenyl)amino]-4-pyrimidinyl trifluoromethanesulfonate (0.0022 mol) and 2,6-dichloro-4-(trifluoromethyl)-benzenamine (0.0044 mol) were combined in 1,4-dioxane (2.5 ml) and heated in a sealed tube under Ar at 170° C. for 40 hours. The reaction mixture was allowed to cool to room temperature. Silica gel was added, and the solvent was evaporated. The residue was purified by flash column chromatography over silica gel (eluent gradient: CH2Cl2:CH3OH:NH4OH 100:0:0 to 97:2.7:0.3). The desired fractions were collected and the solvent was evaporated. The residue was recrystallized from CH3CN, filtered off and dried, yielding 0.086 g (9.2%) of 4-[[4-[[2,6-dichloro-4-(trifluoromethyl)-phenyl]amino]-2-pyrimidinyl]amino]benzonitrile (compound 66).

Workup

  1. temperatureto cool to room temperature
  2. additionSilica gel was added
  3. customthe solvent was evaporated
  4. customThe residue was purified by flash column chromatography over silica gel (eluent gradient: CH2Cl2:CH3OH:NH4OH 100:0:0 to 97:2.7:0.3)
  5. customThe desired fractions were collected
  6. customthe solvent was evaporated
  7. customThe residue was recrystallized from CH3CN
  8. filtrationfiltered off
  9. customdried

Sources & evidence

ORD record
ord-bd145d35e4714fe8bb3911bb5818d553
Source dataset
uspto-grants-2005_06
Patent number
US06903213B2

Reaction notes

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