Piperazine → 3-Benzenesulphonyl-5-methyl-2-methylsulphanyl-7-piperazin-1-yl-pyrazolo[1,5-a]pyrimidine

HRID 636393Notes

Reaction equation

HRID 636393 reaction equation
[NH:1]1[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.Cl[C:8]1[N:13]2[N:14]=[C:15]([S:27][CH3:28])[C:16]([S:17]([C:20]3[CH:25]=[CH:24][C:23](C)=[CH:22][CH:21]=3)(=[O:19])=[O:18])=[C:12]2[N:11]=[C:10]([CH3:29])[CH:9]=1>CN(C=O)C>[C:20]1([S:17]([C:16]2[C:15]([S:27][CH3:28])=[N:14][N:13]3[C:8]([N:1]4[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]4)=[CH:9][C:10]([CH3:29])=[N:11][C:12]=23)(=[O:19])=[O:18])[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

4

Reactant 2

HCID 4837PiperazineHCID 212550447-Chloro-5-methyl-2-methylsulphanyl-3-(toluene-4-sulphonyl)-pyrazolo[1,5-a]pyrimidine

Product 1

HCID 98013133-Benzenesulphonyl-5-methyl-2-methylsulphanyl-7-piperazin-1-yl-pyrazolo[1,5-a]pyrimidineYield 43.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

0.3 g (3.4 mmol) of piperazine in 10 ml of DMF was added to a solution of 0.62 g (1.7 mmol) of 7-chloro-5-methyl-2-methylsulphanyl-3-(toluene-4-sulphonyl)-pyrazolo[1,5-a]pyrimidine in 10 ml of DMF and stirred at 60° for 2 hrs. The reaction solution was cooled to RT and evaporated in a high vacuum. The residue was partitioned between 2N NaOH and CH2Cl2. The aqueous phase was extracted three times with CH2Cl2, and the combined organic phases were dried (MgSO4), filtered and evaporated. Subsequent chromatography (SiO2, CH2Cl2/MeOH 6:1) and crystallization from EtOH yielded 0.30 g (42%) of 3-benzenesulphonyl-5-methyl-2-methylsulphanyl-7-piperazin-1-yl-pyrazolo[1,5-a]pyrimidine as colorless crystals, m.p. 137-139°.

Workup

  1. customevaporated in a high vacuum
  2. customThe residue was partitioned between 2N NaOH and CH2Cl2
  3. extractionThe aqueous phase was extracted three times with CH2Cl2
  4. dry with materialthe combined organic phases were dried (MgSO4)
  5. filtrationfiltered
  6. customevaporated
  7. customSubsequent chromatography (SiO2, CH2Cl2/MeOH 6:1) and crystallization from EtOH

Sources & evidence

ORD record
ord-07b9405cd51e4b279a75f1c5b8e20340
Source dataset
uspto-grants-2001_02
Patent number
US06194410B1

Reaction notes

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