Dimethylamine → HCID 178503608, compound

HRID 636448Notes

Reaction equation

HRID 636448 reaction equation
[CH3:1][NH:2][CH3:3].[C:4]1([S:10]([C:13]2[C:14]([S:25][CH3:26])=[N:15][N:16]3[C:21]([OH:22])=[CH:20][C:19]([CH2:23]Cl)=[N:18][C:17]=23)(=[O:12])=[O:11])[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1>CCO.CN(C=O)C>[C:4]1([S:10]([C:13]2[C:14]([S:25][CH3:26])=[N:15][N:16]3[C:21]([OH:22])=[CH:20][C:19]([CH2:23][N:2]([CH3:3])[CH3:1])=[N:18][C:17]=23)(=[O:12])=[O:11])[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 2

HCID 674DimethylamineHCID 178503603HCID 178503603, compound

Product 1

HCID 178503608HCID 178503608, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6228DimethylformamideSolvent

Procedure

5 ml of a 33% solution of dimethylamine in EtOH were added to a solution of 1.4 g (3.7 mmol) of 3-benzenesulphonyl-5-chloromethyl-2-methylsulphanyl-pyrazolo[1,5-a]pyrimidin-7-ol in 20 ml of DMF and stirred at RT for 4 hrs. The reaction solution was evaporated, the residue was partitioned between 0.5N NaOH and CH2Cl2. The aqueous phase was extracted three times with CH2Cl2. The combined organic phases were dried (MgSO4), filtered and evaporated. Chromatography (SiO2, CH2Cl2/MeOH 4:1) yielded 1.3 g (92%) of 3-benzenesulphonyl-5-dimethylaminomethyl-2-methylsulphanyl-pyrazolo[1,5-a]pyrimidin-7-ol as a beige powder, m.p.>220°.

Workup

  1. customThe reaction solution was evaporated
  2. customthe residue was partitioned between 0.5N 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-55aa8976f7db4b679109d5cc65377d3f
Source dataset
uspto-grants-2001_02
Patent number
US06194410B1

Reaction notes

Loading…