1-Methylpiperazine → 4-Chloro-6-(4-methylpiperazin-1-yl)pyrimidine

HRID 601007Notes

Reaction equation

HRID 601007 reaction equation
Cl[C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[CH:4][N:3]=1.[CH3:9][N:10]1[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]1>C1COCC1>[Cl:8][C:6]1[CH:7]=[C:2]([N:13]2[CH2:14][CH2:15][N:10]([CH3:9])[CH2:11][CH2:12]2)[N:3]=[CH:4][N:5]=1

Participants

4

Reactant 2

HCID 531671-MethylpiperazineHCID 709434,6-Dichloropyrimidine

Product 1

HCID 81780744-Chloro-6-(4-methylpiperazin-1-yl)pyrimidineYield 84.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4,6-dichloropyrimidine, (2 g, 13.4 mmol), and N-methylpiperazine, (1.5 mL, 13.4 mmol), were dissolved in 20 mL THF along with TEA (1.9 mL, 13.4 mmol) and stirred for 18 h. The THF was evaporated and 10 mL water was added and then extracted with DCM. The DCM was dried with sodium sulfate, filtered and evaporated affording 2.4 g of 4-Chloro-6-(4-methyl-piperazin-1-yl)-pyrimidine as a yellow waxy solid which was used without further purification.

Workup

  1. customThe THF was evaporated
  2. addition10 mL water was added
  3. extractionextracted with DCM
  4. dry with materialThe DCM was dried with sodium sulfate
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-2cfa5e8ddfba40f2929cd7f5b546d24f
Source dataset
uspto-grants-2011_03
Patent number
US07902239B2

Reaction notes

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