2,4-Dichloropyrimidine → 5-{[(2-Chloro-4-pyrimidinyl)amino]methyl}-2-{[4-Chloro-3-(trifluoromethyl)phenyl]oxy}benzonitrile

HRID 536155Notes

Reaction equation

HRID 536155 reaction equation
[NH2:1][CH2:2][C:3]1[CH:4]=[CH:5][C:6]([O:11][C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[C:14]([C:19]([F:22])([F:21])[F:20])[CH:13]=2)=[C:7]([CH:10]=1)[C:8]#[N:9].[Cl:23][C:24]1[N:29]=[C:28](Cl)[CH:27]=[CH:26][N:25]=1>CN(C)C=O>[Cl:23][C:24]1[N:29]=[C:28]([NH:1][CH2:2][C:3]2[CH:4]=[CH:5][C:6]([O:11][C:12]3[CH:17]=[CH:16][C:15]([Cl:18])=[C:14]([C:19]([F:22])([F:20])[F:21])[CH:13]=3)=[C:7]([CH:10]=2)[C:8]#[N:9])[CH:27]=[CH:26][N:25]=1

Participants

4

Reactant 2

HCID 775312,4-DichloropyrimidineHCID 66825558HCID 66825558, compound

Product 1

HCID 866970235-{[(2-Chloro-4-pyrimidinyl)amino]methyl}-2-{[4-Chloro-3-(trifluoromethyl)phenyl]oxy}benzonitrileYield 71.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 5-(aminomethyl)-2-{[4-chloro-3-(trifluoromethyl)phenyl]oxy}benzonitrile (500 mg, 1.530 mmol), 2,4-dichloropyrimidine (239 mg, 1.607 mmol) and TEA (1.280 mL, 9.18 mmol) in the N,N-dimethylformamide (5 mL) was stirred at rt overnight. Purification via Biotage-C18 system afforded the title product (480 mg) as a white solid. LC-MS (ESI): m/z 439 [M+H]+; 3.56 min (ret time).

Workup

  1. customPurification via Biotage-C18 system

Sources & evidence

ORD record
ord-f41d361d17b541ddb0e40b9ae3843ab7
Source dataset
uspto-grants-2014_10
Patent number
US08859573B2

Reaction notes

Loading…