N,N-Dimethylethylenediamine → HCID 21254927, compound

HRID 636441Notes

Reaction equation

HRID 636441 reaction equation
[CH3:1][N:2]([CH3:6])[CH2:3][CH2:4][NH2:5].[C:7]1([S:13]([C:16]2[C:17]([S:27][CH3:28])=[N:18][N:19]3[C:24]([NH2:25])=[CH:23][C:22](Cl)=[N:21][C:20]=23)(=[O:15])=[O:14])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1>CN(C=O)C>[C:7]1([S:13]([C:16]2[C:17]([S:27][CH3:28])=[N:18][N:19]3[C:24]([NH2:25])=[CH:4][C:3]([N:2]([CH3:1])[CH3:6])=[N:21][C:20]=23)(=[O:15])=[O:14])[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1.[C:7]1([S:13]([C:16]2[C:17]([S:27][CH3:28])=[N:18][N:19]3[C:24]([NH2:25])=[CH:23][C:22]([NH:5][CH2:4][CH2:3][N:2]([CH3:6])[CH3:1])=[N:21][C:20]=23)(=[O:14])=[O:15])[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

5

Reactant 2

HCID 66053N,N-DimethylethylenediamineHCID 21255038HCID 21255038, compound

Product 2

HCID 21254927HCID 21254927, compoundYield 48%HCID 21255024HCID 21255024, compoundYield 17%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

0.26 g (3 mmol) of 2-dimethylaminoethylamine in 5 ml of DMF was added to a solution of 0.4 g (1 mmol) of 3-benzenesulphonyl-5-chloro-2-methylsulphanyl-pyrazolo[1,5-a]pyrimidin-7-ylamine in 10 ml of DMF and stirred at 90° for 1 hr. The reaction solution was evaporated and the residue was partitioned between H2O and CH2Cl2. The aqueous phase was extracted three times with 50 ml of CH2Cl2. The combined organic phases were dried (MgSO4), filtered and evaporated. Subsequent chromatography (silica gel, CH2Cl2/MeOH 8:1) yielded 0.20 g (48%) of 3-benzenesulphonyl-N5,N5-dimethyl-2-methylsulphanyl-pyrazolo[1,5-a]pyrimidine-5,7-diamine as colorless crystals, m.p.>230°, and 0.08 g (17%) of 3-benzenesulphonyl-N5-(2-dimethylamino-ethyl)-2-methylsulphanyl-pyrazolo[1,5-a]pyrimidine-5,7-diamine as colorless crystals, m.p. 210-212°.

Workup

  1. customThe reaction solution was evaporated
  2. customthe residue was partitioned between H2O and CH2Cl2
  3. extractionThe aqueous phase was extracted three times with 50 ml of CH2Cl2
  4. dry with materialThe combined organic phases were dried (MgSO4)
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-9335b5035d04408bb23621c79897b699
Source dataset
uspto-grants-2001_02
Patent number
US06194410B1

Reaction notes

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