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Sodium hydride → 5-{[(2-Chloro-4-pyrimidinyl)oxy]methyl}-2-{[4-chloro-3-(trifluoromethyl)phenyl]oxy}benzonitrile

HRID 536151
Notes
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Reaction equation

HRID 536151 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9]2[CH:16]=[CH:15][C:14]([CH2:17][OH:18])=[CH:13][C:10]=2[C:11]#[N:12])=[CH:4][C:3]=1[C:19]([F:22])([F:21])[F:20].[H-].[Na+].[Cl:25][C:26]1[N:31]=[C:30](Cl)[CH:29]=[CH:28][N:27]=1>CN(C)C=O>[Cl:25][C:26]1[N:31]=[C:30]([O:18][CH2:17][C:14]2[CH:15]=[CH:16][C:9]([O:8][C:5]3[CH:6]=[CH:7][C:2]([Cl:1])=[C:3]([C:19]([F:20])([F:21])[F:22])[CH:4]=3)=[C:10]([CH:13]=2)[C:11]#[N:12])[CH:29]=[CH:28][N:27]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 775312,4-DichloropyrimidineHCID 668256082-(4-Chloro-3-(trifluoromethyl)phenoxy)-5-(hydroxymethyl)benzonitrile

Product 1

HCID 866970225-{[(2-Chloro-4-pyrimidinyl)oxy]methyl}-2-{[4-chloro-3-(trifluoromethyl)phenyl]oxy}benzonitrileYield 68.8%

Reagents, catalysts & solvents 1

HCID 6228
Dimethylformamide
Solvent

Procedure

To a solution of 2-{[4-chloro-3-(trifluoromethyl)phenyl]oxy}-5-(hydroxymethyl)benzonitrile (2.50 g, 7.63 mmol) in N,N-dimethylformamide (20 mL) was added sodium hydride (1.22 g, 30.5 mmol) at 0° C., then 2,4-dichloropyrimidine (1.25 g, 8.39 mmol) was added at 0° C. after 10 min. The reaction mixture was stirred for 30 min, and poured into ice-water (100 mL), extracted with ethyl acetate (50 mL) twice. Combined organic parts were washed with water and brine, dried over sodium sulfate, filtered and concentrated. Purification via ISCO system afforded the title product (2.31 g). LC-MS (ESI): m/z 440 [M+H]+; 3.95 min (ret time).

Workup

  1. extractionextracted with ethyl acetate (50 mL) twice
  2. washCombined organic parts were washed with water and brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification via ISCO system

Sources & evidence

ORD record
ord-652660ee8cf3470689772fb1a77f002e
Source dataset
uspto-grants-2014_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08859573B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes