Methylamine → 2-Chloro-N-methylpyrimidin-4-amine

HRID 454819Notes

Reaction equation

HRID 454819 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][CH:5]=[C:4](Cl)[N:3]=1.[CH3:9][NH2:10]>CO>[Cl:1][C:2]1[N:3]=[C:4]([NH:10][CH3:9])[CH:5]=[CH:6][N:7]=1

Participants

4

Reactant 2

HCID 6329MethylamineHCID 775312,4-Dichloropyrimidine

Product 1

HCID 137580042-Chloro-N-methylpyrimidin-4-amineYield 27%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2,4-Dichloropyrimidine (104, 500 mg, 3.30 mmol) was dissolved in methanol (5 mL) having 2.0 M monomethylamine 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 evaporated after a treatment with sodium sulfate. Purification was performed by column chromatograph to give the target compound 2-chloro-4-(N-monomethylamino)pyrimidine (106b, 128 mg, 27%) as a yellow 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. customevaporated after a treatment with sodium sulfate
  6. customPurification

Sources & evidence

ORD record
ord-ad322e5b9e474050a91bcd30ded3c982
Source dataset
uspto-grants-2013_07
Patent number
US08497260B2

Reaction notes

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