3-Chloroaniline → Benzyl 2-(3-chlorophenylamino)-4-trifluoromethylpyrimidine-5-carboxylate

HRID 1868368Notes

Reaction equation

HRID 1868368 reaction equation
Cl[C:2]1[N:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[C:5]([C:12]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[O:13])=[CH:4][N:3]=1.[Cl:22][C:23]1[CH:24]=[C:25]([CH:27]=[CH:28][CH:29]=1)[NH2:26]>O1CCOCC1>[Cl:22][C:23]1[CH:24]=[C:25]([NH:26][C:2]2[N:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[C:5]([C:12]([O:14][CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[O:13])=[CH:4][N:3]=2)[CH:27]=[CH:28][CH:29]=1

Participants

4

Reactant 2

HCID 79323-ChloroanilineHCID 2735989Benzyl 2-chloro-4-(trifluoromethyl)pyrimidine-5-carboxylate

Product 1

HCID 16719547Benzyl 2-(3-chlorophenylamino)-4-trifluoromethylpyrimidine-5-carboxylate

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of benzyl 2-chloro-4-trifluoromethylpyrimidine-5-carboxylate (0.50 g, ex Maybridge) in 1,4-dioxan (5 ml) was added 3-chloroaniline (0.85 ml) and the solution stirred at room temperature for 15 h. 1,4-Dioxan was removed under reduced pressure and ethyl acetate (15 ml) added. The solution was washed sequentially with 2N hydrochloric acid (10 ml) and water (3×10 ml), dried (MgSO4), evaporated and triturated with hexane to afford benzyl 2-(3-chlorophenylamino)-4-trifluoromethylpyrimidine-5-carboxylate (524 mg).

Workup

  1. custom1,4-Dioxan was removed under reduced pressure and ethyl acetate (15 ml)
  2. additionadded
  3. washThe solution was washed sequentially with 2N hydrochloric acid (10 ml) and water (3×10 ml)
  4. dry with materialdried (MgSO4)
  5. customevaporated
  6. customtriturated with hexane

Sources & evidence

ORD record
ord-7340782886ed42e89d0a9c3b3ca086f6
Source dataset
uspto-grants-2009_12
Patent number
US07635701B2

Reaction notes

Loading…