Ethanol → HCID 76814745, compound

HRID 1878522Notes

Reaction equation

HRID 1878522 reaction equation
[Br:1][C:2]1[C:3]([C:18]2[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][CH:19]=2)=[N:4][N:5]2[C:10]([N:11]3[CH2:16][CH2:15][O:14][CH2:13][CH2:12]3)=[CH:9][C:8](Cl)=[N:7][C:6]=12.C(=O)([O-])[O-].[K+].[K+].O.[NH2:32][NH2:33].[CH2:34](O)[CH3:35]>>[Br:1][C:2]1[C:3]([C:18]2[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][CH:19]=2)=[N:4][N:5]2[C:10]([N:11]3[CH2:16][CH2:15][O:14][CH2:13][CH2:12]3)=[CH:9][C:8]([NH:32][N:33]=[CH:23][C:18]3[CH:3]=[CH:2][CH:6]=[C:34]([CH3:35])[CH:19]=3)=[N:7][C:6]=12

Participants

5

Reactant 4

HCID 702EthanolHCID 11430Potassium CarbonateHCID 24654Hydrazine hydrate (1:1)HCID 58531057HCID 58531057, compound

Product 1

HCID 76814745HCID 76814745, compound

Conditions

Temperature
150 °C

Procedure

There was suspended, in ethanol (2 mL), 3-bromo-5-chloro-2-(4-methyl-phenyl)-7-morpholin-4-yl-pyrazolo[1,5-a]-pyrimidine (21.7 mg, 0.0532 mM) and then potassium carbonate (9.2 mg, 0.067 mM) and hydrazine monohydrate (13.0 μL, 0.268 mM) were added to the resulting suspension. This suspension was stirred at 150° C. for 10 minutes under the irradiation with microwaves, diluted with a saturated aqueous common salt solution and then extracted with ethyl acetate. The extracts thus obtained were combined, dried over anhydrous sodium sulfate and the solvent was then distilled off. The resulting residue was suspended in ethanol (2 mL), then acetic acid (5.0 μL, 0.087 mM) and 3-methyl-benzaldehyde (13.0 μL, 0.106 mM) were added to the suspension and the resulting mixture was stirred at room temperature for 2 hours. This reaction mixture was filtered and then the resulting solid was purified by the NH-silica gel column chromatography (methylene chloride) to thus give the title compound (6.3 mg, overall yield of these two steps: 23%).

Workup

  1. additiondiluted with a saturated aqueous common salt solution
  2. extractionextracted with ethyl acetate
  3. customThe extracts thus obtained
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationthe solvent was then distilled off
  6. additionacetic acid (5.0 μL, 0.087 mM) and 3-methyl-benzaldehyde (13.0 μL, 0.106 mM) were added to the suspension
  7. stirringthe resulting mixture was stirred at room temperature for 2 hours
  8. filtrationThis reaction mixture was filtered
  9. customthe resulting solid was purified by the NH-silica gel column chromatography (methylene chloride)

Sources & evidence

ORD record
ord-3d0a50b385e3483ebbf0187fdc9bdd99
Source dataset
uspto-grants-2012_11
Patent number
US08314098B2

Reaction notes

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