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

HRID 636413Notes

Reaction equation

HRID 636413 reaction equation
[NH:1]1[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[C:7]1([S:13]([C:16]2[C:17]([S:30][CH3:31])=[N:18][N:19]3[C:24](Cl)=[CH:23][C:22]([C:26]([CH3:29])([CH3:28])[CH3:27])=[N:21][C:20]=23)(=[O:15])=[O:14])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1>CN(C=O)C>[C:7]1([S:13]([C:16]2[C:17]([S:30][CH3:31])=[N:18][N:19]3[C:24]([N:1]4[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]4)=[CH:23][C:22]([C:26]([CH3:27])([CH3:29])[CH3:28])=[N:21][C:20]=23)(=[O:15])=[O:14])[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

4

Reactant 2

HCID 4837PiperazineHCID 212549383-Benzenesulphonyl-5-tert-butyl-7-chloro-2-methylsulphanyl-pyrazolo[1,5-a]pyrimidine

Product 1

HCID 212550543-Benzenesulphonyl-5-tert-butyl-2-methylsulphanyl-7-piperazin-1-yl-pyrazolo[1,5-a]pyrimidineYield 18.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

0.67 g (7.7 mmol) of piperazine in 10 ml of DMF was added to a solution of 1.23 g (3.1 mmol) of 3-benzenesulphonyl-5-tert-butyl-7-chloro-2-methylsulphanyl-pyrazolo[1,5-a]pyrimidine in 10 ml of DMF and stirred at RT for 2 hrs. The reaction solution was evaporated and 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 19:1) and crystallization from EtOH yielded 0.25 g (18%) of 3-benzenesulphonyl-5-tert-butyl-2-methylsulphanyl-7-piperazin-1-yl-pyrazolo[1,5-a]pyrimidine as colorless crystals, m.p. 236-237°.

Workup

  1. customThe reaction solution was evaporated
  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 19:1) and crystallization from EtOH

Sources & evidence

ORD record
ord-803477616bb34276a374d2e2c0fc5b0c
Source dataset
uspto-grants-2001_02
Patent number
US06194410B1

Reaction notes

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