Triethylamine → (6-Chloro-2-phenyl-pyrimidin-4-yl)-(4-trifluoromethoxy-phenyl)-amine

HRID 1161681Notes

Reaction equation

HRID 1161681 reaction equation
Cl[C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[C:4]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[N:3]=1.[F:15][C:16]([F:26])([F:25])[O:17][C:18]1[CH:24]=[CH:23][C:21]([NH2:22])=[CH:20][CH:19]=1.C(N(CC)CC)C>C(O)CCC>[Cl:8][C:6]1[N:5]=[C:4]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[N:3]=[C:2]([NH:22][C:21]2[CH:23]=[CH:24][C:18]([O:17][C:16]([F:15])([F:25])[F:26])=[CH:19][CH:20]=2)[CH:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 77338FenclorimHCID 6008484-(Trifluoromethoxy)aniline

Product 1

HCID 58626074(6-Chloro-2-phenyl-pyrimidin-4-yl)-(4-trifluoromethoxy-phenyl)-amineYield 48.8%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A mixture of compound 4,6-dichloro-2-phenyl-pyrimidine (27 g, 112 mmol), 4-trifluoromethoxy aniline (21 g, 119 mmol) and triethylamine (33 mL, 225 mmol) in n-butanol (300 mL) was refluxed for 20 hours under nitrogen atmosphere. The reaction mixture was then cooled to room temperature and concentrated under vacuum. The crude compound was passed through the silica gel by using 5-6% ethylacetate in petroleum ether to afford the compound (6-chloro-2-phenyl-pyrimidin-4-yl)-(4-trifluoromethoxy-phenyl)-amine (20 g, 46%) as off-white solid.

Workup

  1. temperaturewas refluxed for 20 hours under nitrogen atmosphere
  2. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-4fd8a598cf094e35b81ff1a1002a7f62
Source dataset
uspto-grants-2010_10
Patent number
US07820654B2

Reaction notes

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