Phenol → N-(3-chlorophenyl)-5-(phenoxymethyl)-4-(trifluoromethyl)pyrimidin-2-amine

HRID 38793Notes

Reaction equation

HRID 38793 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]2[N:14]=[C:13]([C:15]([F:18])([F:17])[F:16])[C:12]([CH2:19][OH:20])=[CH:11][N:10]=2)[CH:5]=[CH:6][CH:7]=1.[C:21]1(O)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>ClCCl>[Cl:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]2[N:14]=[C:13]([C:15]([F:17])([F:18])[F:16])[C:12]([CH2:19][O:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[CH:11][N:10]=2)[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 996PhenolHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 58168920[2-(3-Chlorophenylamino)-4-trifluoromethyl-pyrimidin-5-yl]-methanol

Product 1

HCID 58168952N-(3-chlorophenyl)-5-(phenoxymethyl)-4-(trifluoromethyl)pyrimidin-2-amine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of {2-[(3-chlorophenyl)amino]-4-(trifluoromethyl)pyrimidin-5-yl}methanol (200 mg), phenol (70 μL), triphenyl phosphine (190 mg) and dichloromethane (4 mL) was added diethyl azodicarboxylate (330 pt), and the mixture was stirred at room temperature overnight. The reaction mixture was concentrated and the obtained residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate). The obtained pale yellow solid was washed with ethanol-water to obtain N-(3-chlorophenyl)-5-(phenoxymethyl)-4-(trifluoromethyl)pyrimidin-2-amine (55 mg) as a white solid.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe obtained residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate)
  3. washThe obtained pale yellow solid was washed with ethanol-water

Sources & evidence

ORD record
ord-184360825e7740bd8ed2b07419b7ea3e
Source dataset
uspto-grants-2013_09
Patent number
US08524727B2

Reaction notes

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