Sodium Chloride → HCID 66927248, compound

HRID 1026607Notes

Reaction equation

HRID 1026607 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9]2[N:14]=[C:13](Cl)[C:12]([C:16]([F:19])([F:18])[F:17])=[CH:11][N:10]=2)=[CH:4][CH:3]=1.C([N:23](C(C)C)CC)(C)C.CC1CCCO1.[OH-].[Na+].[Cl-].[Na+]>CN1CCCC1=O.C(N(CC)CC)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9]2[N:14]=[C:13]([NH2:23])[C:12]([C:16]([F:19])([F:18])[F:17])=[CH:11][N:10]=2)=[CH:4][CH:3]=1

Participants

8

Reactant 5

HCID 5234Sodium ChlorideHCID 73012-MethyltetrahydrofuranHCID 14798Sodium HydroxideHCID 81531DiisopropylethylamineHCID 86667521HCID 86667521, compound

Product 1

HCID 66927248HCID 66927248, compound

Reagents, catalysts & solvents 2

HCID 8471TriethylamineSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

b-1.) To a suspension or solution of 2-(4-chlorophenyloxy)-4-chloro-5-trifluoromethylpyrimidine (e.g. 1.0 eq) and a suitable inorganic or organic auxiliary base, such as e.g. diisopropylethylamine, triethylamine or an alkali- or earth alkali-metal carbonate (e.g. sodium carbonate, e.g. 5 eq), in a suitable solvent, such as e.g. a solvent described herein as being suitable for nucleophilic aromatic substitution reactions (e.g. 1-methyl-2-pyrrolidinone [NMP]), an appropriate amine of formula V or a suitable salt thereof (e.g. 1.1 eq.) is added at low temperature, e.g. at 0° C. to 5° C. The reaction mixture is stirred under warming up to ambient temperature. The product can be isolated according to procedures familiar to the skilled person. An appropriate organic extractant, e.g. 2-methyl tetrahydrofurane, is added. After clearfiltration (if required), a 1 N sodium hydroxid solution and a saturated sodium chloride solution are added. The organic phase is separated and the solvent is evaporated under reduced pressure. The corresponding crude 2-(4-chlorophenyloxy)-4-amino-5-trifluoromethylpyrimidine derivative of formula IV is obtained as product which may contain NMP as residual solvent.

Workup

  1. customThe product can be isolated
  2. customThe organic phase is separated
  3. customthe solvent is evaporated under reduced pressure

Sources & evidence

ORD record
ord-3727505df8314118b5447affccf929e0
Source dataset
uspto-grants-2014_05
Patent number
US08729265B2

Reaction notes

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