Acetone → 6-Chloro-N-[3-(trifluoromethyl)-phenyl]pyrimidin-4-amine

HRID 1038683Notes

Reaction equation

HRID 1038683 reaction equation
Cl[C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[CH:4][N:3]=1.[NH2:9][C:10]1[CH:11]=[C:12]([C:16]([F:19])([F:18])[F:17])[CH:13]=[CH:14][CH:15]=1.CC(C)=O>O>[Cl:8][C:6]1[N:5]=[CH:4][N:3]=[C:2]([NH:9][C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([C:16]([F:17])([F:18])[F:19])[CH:11]=2)[CH:7]=1

Participants

5

Reactant 3

HCID 180AcetoneHCID 73753-(Trifluoromethyl)anilineHCID 709434,6-Dichloropyrimidine

Product 1

HCID 577809026-Chloro-N-[3-(trifluoromethyl)-phenyl]pyrimidin-4-amine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A stirred mixture of 4,6-dichloropyrimidine (18.6 g, 125 mmol), 3-aminobenzotrifluoride (16.5 mL, 133 mmol), acetone (60 mL) and H2O (90 mL) is kept at reflux for 3 h. Acetone is removed in vacuo, the remaining aqueous layer is basified with conc. aqueous ammonia solution and extracted with ethyl acetate. The organic extract is dried over Na2SO4 and evaporated. The residue is suspended in a small amount of acetone, filtered and the filter cake dried in vacuo to afford the title compound.

Workup

  1. temperatureat reflux for 3 h
  2. customAcetone is removed in vacuo
  3. extractionextracted with ethyl acetate
  4. extractionThe organic extract
  5. dry with materialis dried over Na2SO4
  6. customevaporated
  7. filtrationfiltered
  8. customthe filter cake dried in vacuo

Sources & evidence

ORD record
ord-154d598a0cc54bb9b6949cccd9287608
Source dataset
uspto-grants-2013_10
Patent number
US08552002B2

Reaction notes

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