Morpholine → HCID 178503605, compound

HRID 636455Notes

Reaction equation

HRID 636455 reaction equation
[NH:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[C:7]1([S:13]([C:16]2[C:17]([S:28][CH3:29])=[N:18][N:19]3[C:24]([OH:25])=[CH:23][C:22]([CH2:26]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:28][CH3:29])=[N:18][N:19]3[C:24]([OH:25])=[CH:23][C:22]([CH2:26][N:1]4[CH2:6][CH2:5][O:4][CH2:3][CH2:2]4)=[N:21][C:20]=23)(=[O:14])=[O:15])[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

4

Reactant 2

HCID 8083MorpholineHCID 178503603HCID 178503603, compound

Product 1

HCID 178503605HCID 178503605, compoundYield 88.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1 ml (6 mmol) of morpholine was added to a solution of 2.0 g (5.40 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 and 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 10:1) yielded 2.0 g (88%) of 3-benzenesulphonyl-2-methylsulphanyl-5-morpholin-4-ylmethyl-pyrazolo[1,5-a]pyrimidin-7-ol as a beige foam.

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-d071dcf11cbe4bc5b83c99d81ec455fc
Source dataset
uspto-grants-2001_02
Patent number
US06194410B1

Reaction notes

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