Morpholine → (6-Morpholin-4-yl-2-phenyl-pyrimidin-4-yl)-(4-trifluoromethoxy-phenyl)-amine

HRID 1161682Notes

Reaction equation

HRID 1161682 reaction equation
Cl[C:2]1[N:7]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:5]=[C:4]([NH:14][C:15]2[CH:20]=[CH:19][C:18]([O:21][C:22]([F:25])([F:24])[F:23])=[CH:17][CH:16]=2)[CH:3]=1.[NH:26]1[CH2:31][CH2:30][O:29][CH2:28][CH2:27]1>C(O)CCC>[N:26]1([C:2]2[N:7]=[C:6]([C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=3)[N:5]=[C:4]([NH:14][C:15]3[CH:20]=[CH:19][C:18]([O:21][C:22]([F:25])([F:24])[F:23])=[CH:17][CH:16]=3)[CH:3]=2)[CH2:31][CH2:30][O:29][CH2:28][CH2:27]1

Participants

4

Reactant 2

HCID 8083MorpholineHCID 58626074(6-Chloro-2-phenyl-pyrimidin-4-yl)-(4-trifluoromethoxy-phenyl)-amine

Product 1

HCID 11640285(6-Morpholin-4-yl-2-phenyl-pyrimidin-4-yl)-(4-trifluoromethoxy-phenyl)-amineYield 80.4%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A mixture of compound (6-chloro-2-phenyl-pyrimidin-4-yl)-(4-trifluoromethoxy-phenyl)-amine (39 g, 106 mmol) and morpholine (28 mL, 319 mmol) in n-butanol (400 mL) was refluxed for 24 hours under nitrogen atmosphere. Then the reaction mixture was cooled to room temperature and evaporated under reduced pressure. The crude compound was passed through the silica gel by using 20% ethylacetate in petroleum ether to afford the compound (6-morpholin-4-yl-2-phenyl-pyrimidin-4-yl)-(4-trifluoromethoxy-phenyl)-amine (35.5 g, 80%) as off-white solid.

Workup

  1. temperaturewas refluxed for 24 hours under nitrogen atmosphere
  2. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-6b798a85fe97415895d4c1b2d5aa7cd5
Source dataset
uspto-grants-2010_10
Patent number
US07820654B2

Reaction notes

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