Methanol → N'-{4-[2-(3-chloro-2-methyl-phenoxy)-pyrimidin-4-yloxy]-2,5-dimethyl-phenyl}-N-ethyl-N-methyl-formamidine

HRID 12084Notes

Reaction equation

HRID 12084 reaction equation
[Cl:1][C:2]1[C:3]([CH3:25])=[C:4]([CH:22]=[CH:23][CH:24]=1)[O:5][C:6]1[N:11]=[C:10]([O:12][C:13]2[C:18]([CH3:19])=[CH:17][C:16]([NH2:20])=[C:15]([CH3:21])[CH:14]=2)[CH:9]=[CH:8][N:7]=1.CO.CO[CH:30](OC)[N:31]([CH3:34])[CH2:32][CH3:33]>>[Cl:1][C:2]1[C:3]([CH3:25])=[C:4]([CH:22]=[CH:23][CH:24]=1)[O:5][C:6]1[N:11]=[C:10]([O:12][C:13]2[C:18]([CH3:19])=[CH:17][C:16]([N:20]=[CH:30][N:31]([CH2:32][CH3:33])[CH3:34])=[C:15]([CH3:21])[CH:14]=2)[CH:9]=[CH:8][N:7]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 23017846N-(dimethoxymethyl)-N-methylethanamineHCID 670264424-[2-(3-Chloro-2-methyl-phenoxy)-pyrimidin-4-yloxy]-2,5-dimethyl-phenylamine

Product 1

HCID 16061671N'-{4-[2-(3-chloro-2-methyl-phenoxy)-pyrimidin-4-yloxy]-2,5-dimethyl-phenyl}-N-ethyl-N-methyl-formamidine

Conditions

Temperature
45 °C

Procedure

To a mixture of 293 mg (0.7 mmol) of 4-[2-(3-chloro-2-methyl-phenoxy)-pyrimidin-4-yloxy]-2,5-dimethyl-phenylamine in 20 ml methanol 182 mg (1.05 mmol) of N-(dimethoxymethyl)-N-methyl-ethanamine (77% pure) was added. The reaction mixture was stirred for 20 hrs at 45° C. The reaction mixture was dried over magnesium sulfate concentrated in vacuo and yielded 290 mg (76%) with a purity of 78%; log P (pH 2.3)=2.08.

Workup

  1. additionwas added
  2. dry with materialThe reaction mixture was dried over magnesium sulfate
  3. concentrationconcentrated in vacuo
  4. customyielded 290 mg (76%) with a purity of 78%

Sources & evidence

ORD record
ord-148cb1d56fd049cf839a5bc3d69b3e2b
Source dataset
uspto-grants-2010_06
Patent number
US07727986B2

Reaction notes

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