1-(2-Hydroxyethyl)piperazine → HCID 70001160, compound

HRID 636388Notes

Reaction equation

HRID 636388 reaction equation
[OH:1][CH2:2][CH2:3][N:4]1[CH2:9][CH2:8][NH:7][CH2:6][CH2:5]1.[C:10]1([S:16]([C:19]2[C:20]([S:30][CH3:31])=[N:21][N:22]3[C:27](Cl)=[CH:26][C:25]([CH3:29])=[N:24][C:23]=23)(=[O:18])=[O:17])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>>[C:10]1([S:16]([C:19]2[C:20]([S:30][CH3:31])=[N:21][N:22]3[C:27]([N:7]4[CH2:8][CH2:9][N:4]([CH2:3][CH2:2][OH:1])[CH2:5][CH2:6]4)=[CH:26][C:25]([CH3:29])=[N:24][C:23]=23)(=[O:18])=[O:17])[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

3

Reactant 2

HCID 76771-(2-Hydroxyethyl)piperazineHCID 109810973-Benzenesulphonyl-7-chloro-5-methyl-2-methylsulphanyl-pyrazolo[1,5-a]pyrimidine

Product 1

HCID 70001160HCID 70001160, compoundYield 80.4%

Procedure

0.26 g (2 mmol) of 1(2-hydroxyethyl)-piperazine was added to a solution of 0.35 g (1 mmol) of 3-benzenesulphonyl-7-chloro-5-methyl-2-methylsulphanyl-pyrazolo[1,5 a]pyrimidine 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 he combined organic phases were dried (MgSO4), filtered and evaporated. Subsequent chromatography (SiO2,CH2Cl2/MeOH 19:1) and crystallization from EtOH yielded 0.36 g (73%) of 2-[4(3-benzenesulphonyl-5-methyl-methylsulphanyl-pyrazolo[1,5-a]pyrimidin-7-yl) -piperazin-yl]-ethanol as colorless crystals, m.p. 189-190°.

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, and he
  4. dry with materialwere dried (MgSO4)
  5. filtrationfiltered
  6. customevaporated
  7. customSubsequent chromatography (SiO2,CH2Cl2/MeOH 19:1) and crystallization from EtOH

Sources & evidence

ORD record
ord-936c09be4351469a9a1dc2c4e6b98a05
Source dataset
uspto-grants-2001_02
Patent number
US06194410B1

Reaction notes

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