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

HRID 12086Notes

Reaction equation

HRID 12086 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

4

Reactant 3

HCID 6342AcetonitrileHCID 23017846N-(dimethoxymethyl)-N-methylethanamineHCID 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.

Workup

  1. additionwas added
  2. temperatureThe reaction mixture was refluxed for 20 hrs
  3. concentrationThe reaction mixture was concentrated in vacuo
  4. additiondiluted with ethyl acetate
  5. washwashed with water
  6. dry with materialThe organic layer was dried over magnesium sulfate
  7. concentrationconcentrated in vacuo
  8. customyielded 220 mg (59%) with a purity of 72% log P (pH=2.3)=1.45

Sources & evidence

ORD record
ord-7ccb126b89ca40838648d5c99efc243b
Source dataset
uspto-grants-2010_06
Patent number
US07727986B2

Reaction notes

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