Imidazole → HCID 21255017, compound

HRID 636386Notes

Reaction equation

HRID 636386 reaction equation
C[O-].[Na+].[NH:4]1[CH:8]=[CH:7][N:6]=[CH:5]1.[C:9]1([S:15]([C:18]2[C:19]([S:29][CH3:30])=[N:20][N:21]3[C:26](Cl)=[CH:25][C:24]([CH3:28])=[N:23][C:22]=23)(=[O:17])=[O:16])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>CN(C=O)C>[C:9]1([S:15]([C:18]2[C:19]([S:29][CH3:30])=[N:20][N:21]3[C:26]([N:4]4[CH:8]=[CH:7][N:6]=[CH:5]4)=[CH:25][C:24]([CH3:28])=[N:23][C:22]=23)(=[O:17])=[O:16])[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 10942334Sodium MethoxideHCID 109810973-Benzenesulphonyl-7-chloro-5-methyl-2-methylsulphanyl-pyrazolo[1,5-a]pyrimidine

Product 1

HCID 21255017HCID 21255017, compoundYield 51.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

0.08 g (1.5 mmol) of sodium methanolate was added to a suspension of 0.122 g (1.8 mmol) of imidazole in 30 ml of DMF and stirred at 60° for 15 min. Subsequently, a solution of 0.53 g (1.5 mmol) of 3-benzenesulphonyl-7-chloro-5-methyl-2-methylsulphanyl-pyrazolo[1,5-a]-pyrimidine in 10 ml of DMF was added to this suspension and stirred at 60° for 1 hr. 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 15:1) and crystallization from EtOH yielded 0.30 g (51%) of 3-benzenesulphonyl-7-imidazol-1-yl-5-methyl-2-methylsulphanyl-pyrazolo[1,5-a]pyrimidine as colorless crystal, m.p. >230°.

Workup

  1. stirringstirred at 60° for 1 hr
  2. customevaporated in a high vacuum
  3. customThe residue was partitioned between 2N NaOH and CH2Cl2
  4. extractionThe aqueous phase was extracted three times with CH2Cl2
  5. dry with materialthe combined organic phases were dried (MgSO4)
  6. filtrationfiltered
  7. customevaporated
  8. customSubsequent chromatography (SiO2, CH2Cl2/MeOH 15:1) and crystallization from EtOH

Sources & evidence

ORD record
ord-b170bbb24471453aa4381319779e6a84
Source dataset
uspto-grants-2001_02
Patent number
US06194410B1

Reaction notes

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