Dimethylamine → 2-Chloro-N,N-dimethylpyrimidin-4-amine

HRID 454820

Reaction equation

HRID 454820 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][CH:5]=[C:4](Cl)[N:3]=1.[CH3:9][NH:10][CH3:11]>CO>[Cl:1][C:2]1[N:3]=[C:4]([N:10]([CH3:11])[CH3:9])[CH:5]=[CH:6][N:7]=1

Participants

4

Procedure

2,4-dichloropyrimidine (104, 500 mg, 3.30 mmol) was dissolved in methanol (5 mL) having 2.0 M dimethylamine dissolved therein, stirred at room temperature for 3 hours. Then, the methanol solvent was removed under reduced pressure and water was added to the reaction mixture. Organic compounds were extracted with ethyl acetate, and the recovered organic solution was washed with a saturated aqueous solution of sodium chloride and evaporated after a treatment with sodium sulfate. Purification was performed by column chromatograph to give the target compound 2-chloro-4-(N,N-dimethylamino)pyrimidine (106c, 426 mg, 80%) as a white solid.

Workup

  1. dissolutiondissolved
  2. customThen, the methanol solvent was removed under reduced pressure and water
  3. additionwas added to the reaction mixture
  4. extractionOrganic compounds were extracted with ethyl acetate
  5. washthe recovered organic solution was washed with a saturated aqueous solution of sodium chloride
  6. customevaporated after a treatment with sodium sulfate
  7. customPurification

Sources & evidence

ORD record
ord-8a5b2f72baff42b985b64400774426b0
Source dataset
uspto-grants-2013_07
Patent number
US08497260B2

Linked notes

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