Morpholine → 5-Chloro-7-morpholin-4-yl-3-phenyl-pyrazolo[1,5-a]pyrimidine

HRID 1878524Notes

Reaction equation

HRID 1878524 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6](Cl)[N:5]2[N:9]=[CH:10][C:11]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[C:4]2[N:3]=1.[NH:18]1[CH2:23][CH2:22][O:21][CH2:20][CH2:19]1>O1CCOCC1>[Cl:1][C:2]1[CH:7]=[C:6]([N:18]2[CH2:23][CH2:22][O:21][CH2:20][CH2:19]2)[N:5]2[N:9]=[CH:10][C:11]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[C:4]2[N:3]=1

Participants

4

Reactant 2

HCID 8083MorpholineHCID 134659465,7-Dichloro-3-phenylpyrazolo[1,5-a]pyrimidine

Product 1

HCID 585311525-Chloro-7-morpholin-4-yl-3-phenyl-pyrazolo[1,5-a]pyrimidineYield 82%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

There was dissolved, in 1,4-dioxane (2 mL), 5,7-dichloro-3-phenyl-pyrazolo-[1,5-a]pyrimidine (47.7 mg, 0.181 mM), then morpholine (31.6 μL, 0.362 mM) was added to the solution and the resulting mixture was stirred at room temperature for 30 minutes. The solvent was distilled off from this 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, the solvent was then distilled off, and the resulting solid was washed with methanol to thus obtain the title compound (46.8 mg, yield: 82%).

Workup

  1. distillationThe solvent was distilled off from this 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
  7. washthe resulting solid was washed with methanol

Sources & evidence

ORD record
ord-367618bb276044539d6052317857ad8c
Source dataset
uspto-grants-2012_11
Patent number
US08314098B2

Reaction notes

Loading…