Acetonitrile → N'-{4-[(2-chloro-6-methylpyrimidin-4-yl)oxy]-2,5-dimethylphenyl}-N-ethyl-N-methylimido-formamide

Reaction equation

[Cl:1][C:2]1[N:7]=[C:6]([O:8][C:9]2[C:15]([CH3:16])=[CH:14][C:12]([NH2:13])=[C:11]([CH3:17])[CH:10]=2)[CH:5]=[C:4]([CH3:18])[N:3]=1.C(#N)C.CO[CH:24](OC)[N:25]([CH3:28])[CH2:26][CH3:27]>>[Cl:1][C:2]1[N:7]=[C:6]([O:8][C:9]2[C:15]([CH3:16])=[CH:14][C:12]([N:13]=[CH:24][N:25]([CH2:26][CH3:27])[CH3:28])=[C:11]([CH3:17])[CH:10]=2)[CH:5]=[C:4]([CH3:18])[N:3]=1

Participants

Reactant 3

HCID 6342Acetonitrile

HCID 23017846N-(dimethoxymethyl)-N-methylethanamine

HCID 866289754-[(2-Chloro-6-methylpyrimidin-4-yl)oxy]-2,5-dimethylaniline

Product 1

HCID 16061672N'-{4-[(2-chloro-6-methylpyrimidin-4-yl)oxy]-2,5-dimethylphenyl}-N-ethyl-N-methylimido-formamide

Procedure

To a mixture of 310 mg (0.8 mmol) of 4-[(2-chloro-6-methylpyrimidin-4-yl)oxy]-2,5-dimethyl-aniline in 20 ml acetonitrile 208 mg (1.5 mmol) of N-(dimethoxymethyl)-N-methylethanamine (77% pure) was added. The reaction mixture was refluxed for 20 hrs. The reaction mixture was concentrated in vacuo, diluted with ethyl acetate and washed with water. The organic layer was dried over magnesium sulfate and concentrated in vacuo yielded 220 mg (59%) with a purity of 72% log P (pH=2.3)=1.45.