4-Chloro-2-toluidine → 2-(2-Methyl-4-chloro-phenylamino)-4-trifluoromethyl-pyrimidine-5-carboxylic acid cyclobutylmethyl-amide

HRID 1868399Notes

Reaction equation

HRID 1868399 reaction equation
[CH:1]1([CH2:5][NH:6][C:7]([C:9]2[C:10]([C:16]([F:19])([F:18])[F:17])=[N:11][C:12](Cl)=[N:13][CH:14]=2)=[O:8])[CH2:4][CH2:3][CH2:2]1.[CH3:20][C:21]1[CH:27]=[C:26]([Cl:28])[CH:25]=[CH:24][C:22]=1[NH2:23]>O1CCOCC1.CS(C)=O>[CH:1]1([CH2:5][NH:6][C:7]([C:9]2[C:10]([C:16]([F:19])([F:18])[F:17])=[N:11][C:12]([NH:23][C:22]3[CH:24]=[CH:25][C:26]([Cl:28])=[CH:27][C:21]=3[CH3:20])=[N:13][CH:14]=2)=[O:8])[CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 72514-Chloro-2-toluidineHCID 579826652-Chloro-4-trifluoromethyl-pyrimidin-5-carboxylic acid cyclobutylmethyl-amide

Product 1

HCID 579825792-(2-Methyl-4-chloro-phenylamino)-4-trifluoromethyl-pyrimidine-5-carboxylic acid cyclobutylmethyl-amideYield 53%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
180 °C

Procedure

To a solution of 2-chloro-4-trifluoromethyl-pyrimidin-5-carboxylic acid cyclobutylmethyl-amide (50 mg) in 1,4-dioxan (1.0 ml) was added 2-methyl-4-chloroaniline (120 mg) and the solution heated at 180° C. under microwave irrdiation for 30×2 minutes. The residue was dissolved in 1:1 DMSO:methanol (11.0 ml) and purified by Mass Directed Auto-Purification to afford the title compound (36 mg).

Workup

  1. custommethanol (11.0 ml) and purified by Mass Directed Auto-Purification

Sources & evidence

ORD record
ord-98cefdb5e4b240419b70b4f68837de05
Source dataset
uspto-grants-2009_12
Patent number
US07635701B2

Reaction notes

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