Morpholine → 2-(1-Benzyloxy-carbonyl-piperidin-4-yl)-5-chloro-7-morpholin-4-yl-pyrazolo[1,5-a]pyrimidine

HRID 1878583Notes

Reaction equation

HRID 1878583 reaction equation
[CH2:1]([O:8][N:9]1[CH2:14][CH2:13][CH:12]([C:15]2[CH:25]=[C:18]3[N:19]=[C:20]([Cl:24])[CH:21]=[C:22](Cl)[N:17]3[N:16]=2)[CH2:11][C:10]1=[C:26]=[O:27])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH:28]1[CH2:33][CH2:32][O:31][CH2:30][CH2:29]1>O1CCOCC1.O>[CH2:1]([O:8][N:9]1[CH2:14][CH2:13][CH:12]([C:15]2[CH:25]=[C:18]3[N:19]=[C:20]([Cl:24])[CH:21]=[C:22]([N:28]4[CH2:33][CH2:32][O:31][CH2:30][CH2:29]4)[N:17]3[N:16]=2)[CH2:11][C:10]1=[C:26]=[O:27])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 8083MorpholineHCID 866597322-(1-Benzyloxy-carbonyl-piperidin-4-yl)-5,7-dichloro-pyrazolo[1,5-a]-pyrimidine

Product 1

HCID 866597312-(1-Benzyloxy-carbonyl-piperidin-4-yl)-5-chloro-7-morpholin-4-yl-pyrazolo[1,5-a]pyrimidineYield 88%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

There was dissolved, in 1,4-dioxane (5 mL), 2-(1-benzyloxy-carbonyl-piperidin-4-yl)-5,7-dichloro-pyrazolo[1,5-a]-pyrimidine (192 mg, 0.474 mM), then morpholine (82.7 μL, 0.948 mM) was added to the solution and the mixture was stirred at room temperature for one hour. The solvent was distilled off from this reaction mixture, the residue thus obtained was diluted with water and then the mixture was extracted with ethyl acetate. The resulting extracts were combined, dried over anhydrous sodium sulfate, the solvent was distilled off and the resulting solid was washed with diethyl ether to thus give the title compound (191 mg, yield: 88%).

Workup

  1. distillationThe solvent was distilled off from this reaction mixture
  2. customthe residue thus obtained
  3. extractionthe mixture was extracted with ethyl acetate
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationthe solvent was distilled off
  6. washthe resulting solid was washed with diethyl ether

Sources & evidence

ORD record
ord-a295b00352dd477e87bbc62737850594
Source dataset
uspto-grants-2012_11
Patent number
US08314098B2

Reaction notes

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