Ammonia → HCID 21254933, compound

HRID 636450Notes

Reaction equation

HRID 636450 reaction equation
[NH3:1].[C:2]1([S:8]([C:11]2[C:12]([S:25][CH3:26])=[N:13][N:14]3[C:19](Cl)=[CH:18][C:17]([CH2:21][N:22]([CH3:24])[CH3:23])=[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:25][CH3:26])=[N:13][N:14]3[C:19]([NH2:1])=[CH:18][C:17]([CH2:21][N:22]([CH3:24])[CH3:23])=[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 21255050HCID 21255050, compound

Product 1

HCID 21254933HCID 21254933, compoundYield 78%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

20 ml of a 50% solution of NH3 in MeOH were added to a solution of 1.20 g (3 mmol) of (3-benzenesulphonyl-7-chloro-2-methylsulphanyl-pyrazolo[1,5-a]pyrimidin-5-ylmethyl)-dimethyl-amine in 30 ml of DMF and stirred at RT for 4 hrs. The reaction solution was evaporated 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 6:1) yielded 0.90 g (78%) of 3-benzenesulphonyl-5-dimethylaminomethyl-2-methylsulphanyl-pyrazolo[1,5-a]pyrimidin-7-ylamine as colorless crystals, m.p. 216-218°.

Workup

  1. customThe reaction solution was evaporated
  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

Sources & evidence

ORD record
ord-dc644a8f88e242f18f27796749c707a7
Source dataset
uspto-grants-2001_02
Patent number
US06194410B1

Reaction notes

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