Methylamine → (3-Benzenesulphonyl 5-methyl-2-methylsulphanyl-pyrazolo[1,5-a]pyrimidin-7-yl)-methyl-amine

HRID 636383Notes

Reaction equation

HRID 636383 reaction equation
[CH3:1][NH2:2].[C:3]1([S:9]([C:12]2[C:13]([S:23][CH3:24])=[N:14][N:15]3[C:20](Cl)=[CH:19][C:18]([CH3:22])=[N:17][C:16]=23)(=[O:11])=[O:10])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1>CCO.CN(C=O)C>[C:3]1([S:9]([C:12]2[C:13]([S:23][CH3:24])=[N:14][N:15]3[C:20]([NH:2][CH3:1])=[CH:19][C:18]([CH3:22])=[N:17][C:16]=23)(=[O:11])=[O:10])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

5

Reactant 2

HCID 6329MethylamineHCID 109810973-Benzenesulphonyl-7-chloro-5-methyl-2-methylsulphanyl-pyrazolo[1,5-a]pyrimidine

Product 1

HCID 9928283(3-Benzenesulphonyl 5-methyl-2-methylsulphanyl-pyrazolo[1,5-a]pyrimidin-7-yl)-methyl-amineYield 60%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6228DimethylformamideSolvent

Procedure

10 ml of a 33% solution of methylamine in EtOH was added to a solution of 0.3 g (0.85 mmol) of 3-benzenesulphonyl-7-chloro-5-methyl-2-methylsulphanyl-pyrazolo[1,5-a]pyrimidine in 5 ml of DMF and stirred at RT for 2 hrs. The reaction solution was evaporated in a high vacuum 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/AcOEt 15:1) and crystallization from EtOH yielded 0.18 g (60%) of (3-benzenesulphonyl 5-methyl-2-methylsulphanyl-pyrazolo[1,5-a]pyrimidin-7-yl)-methyl-amine as colorless crystals, m.p. >230°.

Workup

  1. customThe reaction solution was evaporated 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/AcOEt 15:1) and crystallization from EtOH

Sources & evidence

ORD record
ord-a2c451f8b2454a74b711e2734ae6780f
Source dataset
uspto-grants-2001_02
Patent number
US06194410B1

Reaction notes

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