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

HRID 636384Notes

Reaction equation

HRID 636384 reaction equation
[NH3:1].[C:2]1([S:8]([C:11]2[C:12]([S:22][CH3:23])=[N:13][N:14]3[C:19](Cl)=[CH:18][C:17]([CH3:21])=[N:16][C:15]=23)(=[O:10])=[O:9])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>CO.CN(C=O)C>[C:2]1([S:8]([C:11]2[C:12]([S:22][CH3:23])=[N:13][N:14]3[C:19]([NH2:1])=[CH:18][C:17]([CH3:21])=[N:16][C:15]=23)(=[O:10])=[O:9])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 222AmmoniaHCID 109810973-Benzenesulphonyl-7-chloro-5-methyl-2-methylsulphanyl-pyrazolo[1,5-a]pyrimidine

Product 1

HCID 9797773(3-Benzenesulphonyl-5-methyl-2-methylsulphanyl-pyrazolo[1,5-a]pyrimidin-7-yl)amineYield 66%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

10 ml of a 50% solution of NH3 in MeOH were added to a solution of 0.40 g (1.13 mmol) of 3-benzenesulphonyl-7-chloro-5-methyl-2-methylsulphanyl-pyrazolo[1,5-a]pyrimidine in 10 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 7:1) and crystallization from EtOH yielded 0.25 g (66%) of (3-benzenesulphonyl-5-methyl-2-methylsulphanyl-pyrazolo[1,5-a]pyrimidin-7-yl)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 7:1) and crystallization from EtOH

Sources & evidence

ORD record
ord-7d039ff539e74d68810908de93fe9446
Source dataset
uspto-grants-2001_02
Patent number
US06194410B1

Reaction notes

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