Morpholine → 5-Chloro-7-morpholin-4-yl-pyrazolo[1,5-a]pyrimidine

HRID 1878527Notes

Reaction equation

HRID 1878527 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6](Cl)[N:5]2[N:9]=[CH:10][CH:11]=[C:4]2[N:3]=1.[NH:12]1[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1>O1CCOCC1>[Cl:1][C:2]1[CH:7]=[C:6]([N:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)[N:5]2[N:9]=[CH:10][CH:11]=[C:4]2[N:3]=1

Participants

4

Reactant 2

HCID 8083MorpholineHCID 110741545,7-Dichloropyrazolo[1,5-a]pyrimidine

Product 1

HCID 585310715-Chloro-7-morpholin-4-yl-pyrazolo[1,5-a]pyrimidineYield 91%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

5,7-Dichloro-pyrazolo[1,5-a]pyrimidine (400 mg, 2.13 mM) was dissolved in 1,4-dioxane (8 mL), then morpholine (372 μL, 4.26 mM) was added to the solution and the mixture was stirred at room temperature for 30 minutes. The solvent was distilled off from the reaction mixture, the resulting residue was diluted with water and extracted with methylene chloride. The extracts thus obtained were combined, dried over anhydrous sodium sulfate and the solvent was then distilled off to give the title compound (461 mg, yield: 91%).

Workup

  1. distillationThe solvent was distilled off from the reaction mixture
  2. additionthe resulting residue was diluted with water
  3. extractionextracted with methylene chloride
  4. customThe extracts thus obtained
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationthe solvent was then distilled off

Sources & evidence

ORD record
ord-73269f080580408ba8db7cd5f0989e66
Source dataset
uspto-grants-2012_11
Patent number
US08314098B2

Reaction notes

Loading…