Ammonia → 3-Benzenesulphonyl-5-(4-methyl-piperazin-1-ylmethyl)-2-methylsulphanyl-pyrazolo[1,5-a]pyrimidin-7-ylamine

HRID 636456Notes

Reaction equation

HRID 636456 reaction equation
[NH3:1].[C:2]1([S:8]([C:11]2[C:12]([S:28][CH3:29])=[N:13][N:14]3[C:19](Cl)=[CH:18][C:17]([CH2:21][N:22]4[CH2:27][CH2:26]O[CH2:24][CH2:23]4)=[N:16][C:15]=23)(=[O:10])=[O:9])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[N:31]([CH:33]=O)C>CO>[C:2]1([S:8]([C:11]2[C:12]([S:28][CH3:29])=[N:13][N:14]3[C:19]([NH2:1])=[CH:18][C:17]([CH2:21][N:22]4[CH2:27][CH2:26][N:31]([CH3:33])[CH2:24][CH2:23]4)=[N:16][C:15]=23)(=[O:10])=[O:9])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 6228DimethylformamideHCID 212549113-Benzenesulphonyl-7-chloro-2-methylsulphanyl-5-morpholin-4-ylmethyl-pyrazolo[1,5-a]pyrimidine

Product 1

HCID 212550223-Benzenesulphonyl-5-(4-methyl-piperazin-1-ylmethyl)-2-methylsulphanyl-pyrazolo[1,5-a]pyrimidin-7-ylamineYield 83%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

10 ml of a 50% solution of NH3 in MeOH were added to a solution of 0.9 g (2 mmol) of 3-benzenesulphonyl-7-chloro-2-methylsulphanyl-5-morpholin-4-ylmethyl-pyrazolo[1,5-a]pyrimidine in 20 DMF and stirred at RT for 4 hrs. The DMF 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 (silica gel, CH2Cl2/MeOH/NH4OH 80:10:1) and crystallization from EtOH yielded 0.70 g (83%) of 3-benzenesulphonyl-5-(4-methyl-piperazin-1-ylmethyl)-2-methylsulphanyl-pyrazolo[1,5-a]pyrimidin-7-ylamine as colorless crystals, m.p. 224-226°.

Workup

  1. customThe DMF 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 (silica gel, CH2Cl2/MeOH/NH4OH 80:10:1) and crystallization from EtOH

Sources & evidence

ORD record
ord-d072ac4471944b73b435aef01598b678
Source dataset
uspto-grants-2001_02
Patent number
US06194410B1

Reaction notes

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