Ethanol → HCID 75216467, compound

HRID 1878540Notes

Reaction equation

HRID 1878540 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][C:20]([N:23]4[CH2:28][CH2:27][O:26][CH2:25][CH2:24]4)=[CH:19][CH:18]=3)[CH:16]=[C:4]2[N:3]=1.C(=O)([O-])[O-].[K+].[K+].O.[NH2:36][NH2:37].[CH2:38](O)[CH3:39]>>[CH3:4][C:16]1[CH:15]=[C:17]([CH:18]=[CH:38][CH:39]=1)[CH:22]=[N:36][NH:37][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][C:20]([N:23]4[CH2:28][CH2:27][O:26][CH2:25][CH2:24]4)=[CH:19][CH:18]=3)[CH:16]=[C:4]2[N:3]=1

Participants

5

Reactant 4

HCID 702EthanolHCID 11430Potassium CarbonateHCID 24654Hydrazine hydrate (1:1)HCID 58531075HCID 58531075, compound

Product 1

HCID 75216467HCID 75216467, compound

Conditions

Temperature
150 °C

Procedure

There was suspended, in ethanol (2 mL), 5-chloro-7-morpholin-4-yl-2-(4-morpholin-4-yl-phenyl)-pyrazolo[1,5-a]-pyrimidine (36.3 mg, 0.0908 mM) and then potassium carbonate (13.8 mg, 0.0999 mM) and hydrazine monohydrate (44.0 μL, 0.908 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, dried over anhydrous sodium sulfate and then 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 (10.7 μL, 0.0908 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 (23.8 mg, overall yield of these two steps: 49%).

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 (10.7 μL, 0.0908 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-76cae81d776b4d538f1d2f7463e7fc4e
Source dataset
uspto-grants-2012_11
Patent number
US08314098B2

Reaction notes

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