Ethanol → HCID 76814773, compound

HRID 1878534Notes

Reaction equation

HRID 1878534 reaction equation
Cl[C:2]1[CH:7]=[C:6]([N:8]2[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)[N:5]2[N:14]=[C:15]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[CH3:23])[CH:16]=[C:4]2[N:3]=1.C(=O)([O-])[O-].[K+].[K+].O.[NH2:31][NH2:32].[CH2:33](O)[CH3:34]>>[CH3:4][C:16]1[CH:15]=[C:17]([CH:18]=[CH:33][CH:34]=1)[CH:22]=[N:31][NH:32][C:2]1[CH:7]=[C:6]([N:8]2[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)[N:5]2[N:14]=[C:15]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[CH3:23])[CH:16]=[C:4]2[N:3]=1

Participants

5

Reactant 4

HCID 702EthanolHCID 11430Potassium CarbonateHCID 24654Hydrazine hydrate (1:1)HCID 58531138HCID 58531138, compound

Product 1

HCID 76814773HCID 76814773, compound

Conditions

Temperature
150 °C

Procedure

There was suspended, in ethanol (2 mL), 5-chloro-2-(2-methyl-phenyl)-7-morpholin-4-yl-pyrazolo[1,5-a]pyrimidine (72.1 mg, 0.219 mM) and then potassium carbonate (32.8 mg, 0.241 mM) and hydrazine monohydrate (106 μL, 2.19 mM) were added to the suspension. This suspension was stirred at 150° C. for 20 minutes under the irradiation with microwaves. This reaction liquid was diluted with a saturated aqueous common salt solution and then extracted with ethyl acetate. The extracts thus obtained were combined together and then dried over anhydrous sodium sulfate and the solvent was distilled off. The resulting residue was suspended in ethanol (2 mL), then acetic acid (5.0 μL, 0.087 mM) and 3-methyl-benzaldehyde (25.4 μL, 0.219 mM) were added to the suspension and the mixture was stirred at room temperature for one hour. This reaction mixture was filtered and the resulting solid was purified by the NH-silica gel column chromatography (methylene chloride) to give the title compound (11.2 mg, overall yield of these two steps: 12%).

Workup

  1. customThis reaction liquid
  2. additionwas diluted with a saturated aqueous common salt solution
  3. extractionextracted with ethyl acetate
  4. customThe extracts thus obtained
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationthe solvent was distilled off
  7. additionacetic acid (5.0 μL, 0.087 mM) and 3-methyl-benzaldehyde (25.4 μL, 0.219 mM) were added to the suspension
  8. stirringthe mixture was stirred at room temperature for one hour
  9. filtrationThis reaction mixture was filtered
  10. customthe resulting solid was purified by the NH-silica gel column chromatography (methylene chloride)

Sources & evidence

ORD record
ord-22d9e6c7f72047f1a2036cb9d8380209
Source dataset
uspto-grants-2012_11
Patent number
US08314098B2

Reaction notes

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