Chloromethyl methyl sulfide → HCID 13210510, compound

HRID 1462239Notes

Reaction equation

HRID 1462239 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([NH:21][C:22]3[N:27]=[CH:26][CH:25]=[CH:24][N:23]=3)=[CH:17][CH:16]=2)[C:10](=[O:28])[C:9]1=[O:29])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].Cl[CH2:33][S:34][CH3:35]>CN(C)C=O>[CH2:1]([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([N:21]([CH2:33][S:34][CH3:35])[C:22]3[N:23]=[CH:24][CH:25]=[CH:26][N:27]=3)=[CH:17][CH:16]=2)[C:10](=[O:28])[C:9]1=[O:29])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 16916Chloromethyl methyl sulfideHCID 24758Sodium hydrideHCID 30602472,3-Piperazinedione, 1-(phenylmethyl)-4-((4-(2-pyrimidinylamino)phenyl)methyl)-

Product 1

HCID 13210510HCID 13210510, compoundYield 86.45%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In 40 ml of N,N-dimethylformamide was dissolved 3.0 g of 1-benzyl-4-[4-(2-pyrimidinylamino)benzyl]-2,3-dioxopiperazine, and 0.372 g of sodium hydride (purity 52%) was added thereto, after which the resulting mixture was subjected to reaction at 80° C. for 30 min. with stirring. The reaction mixture was then cooled, and 0.72 ml of chloromethylmethylsulfide was added thereto, after which the resulting mixture was subjected to reaction at 50° to 60° C. for 2 hours. After the completion of the reaction, the reaction mixture was distilled under reduced pressure and the residue thus obtained was extracted with chloroform and then washed with water. The solution thus obtained was dried over anhydrous magnesium sulfate, and the solvent was then removed by distillation under reduced pressure. The crystals thus obtained were recrystallized from isopropyl alcohol to obtain 3.0 g (86.45% yield) of white crystalline 1-benzyl-4-{4-[N-methylthiomethyl-N-(2-pyrimidinyl)amino]benzyl}-2,3-dioxopiperazine having a melting point of 156° C.

Workup

  1. additionwas added
  2. customafter which the resulting mixture was subjected to reaction at 80° C. for 30 min.
  3. temperatureThe reaction mixture was then cooled
  4. customafter which the resulting mixture was subjected to reaction at 50° to 60° C. for 2 hours
  5. customAfter the completion of the reaction
  6. distillationthe reaction mixture was distilled under reduced pressure
  7. customthe residue thus obtained
  8. extractionwas extracted with chloroform
  9. washwashed with water
  10. customThe solution thus obtained
  11. dry with materialwas dried over anhydrous magnesium sulfate
  12. customthe solvent was then removed by distillation under reduced pressure
  13. customThe crystals thus obtained
  14. customwere recrystallized from isopropyl alcohol

Sources & evidence

ORD record
ord-d41476b81c0e4a44a2f5b2d9067aa6c3
Source dataset
uspto-grants-1984_07
Patent number
US04459407

Reaction notes

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