Hydrazine hydrate (1:1) → HCID 178490035, compound

HRID 2390772Notes

Reaction equation

HRID 2390772 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:10](=O)[CH2:11][C:12]2[CH:17]=[CH:16][N:15]=[C:14]([S:18][CH3:19])[N:13]=2)[CH:6]=[C:7]([CH3:9])[CH:8]=1.COC(OC)[N:24]([CH3:26])C.O.[NH2:30]N>>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:10]2[C:11]([C:12]3[CH:17]=[CH:16][N:15]=[C:14]([S:18][CH3:19])[N:13]=3)=[CH:26][NH:24][N:30]=2)[CH:6]=[C:7]([CH3:9])[CH:8]=1

Participants

4

Reactant 3

HCID 24654Hydrazine hydrate (1:1)HCID 78373Dimethylformamide dimethyl acetalHCID 508989391-(3-Methoxy-5-methylphenyl)-2-(2-(methylthio)pyrimidin-4-yl)ethanone

Product 1

HCID 178490035HCID 178490035, compoundYield 78.6%

Procedure

1-(3-Methoxy-5-methylphenyl)-2-(2-(methylthio)pyrimidin-4-yl)ethanone was heated with N,N-dimethylformamide dimethylacetal (34.46 mL, 258.6 mmol) at 90° C. for 20 hours with stirring. Excess N,N-dimethylformamide dimethylacetal was removed by vacuum distillation, and the reaction mixture was dissolved in anhydrous ethanol (55 mL). To this solution was dropwise added hydrazine hydrate (2.59 mL, 51.72 mmol), and stirred at room temperature for 12 hours. After completion of the cyclization, the solvent was removed by vacuum distillation. The concentrate was treated in water and ethyl acetate, and the organic layer was dried over anhydrous magnesium sulfate, filtered and distilled under vacuum. Purification by column chromatography gave the title compound (6.35 g, 78.6%).

Workup

  1. customExcess N,N-dimethylformamide dimethylacetal was removed by vacuum distillation
  2. dissolutionthe reaction mixture was dissolved in anhydrous ethanol (55 mL)
  3. stirringstirred at room temperature for 12 hours
  4. customAfter completion of the cyclization, the solvent was removed by vacuum distillation
  5. additionThe concentrate was treated in water
  6. dry with materialethyl acetate, and the organic layer was dried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. distillationdistilled under vacuum
  9. customPurification by column chromatography

Sources & evidence

ORD record
ord-aa6270d22af2431185d5f409187206c5
Source dataset
uspto-grants-2012_09
Patent number
US08273880B2

Reaction notes

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