Water → HCID 21460366, compound

HRID 1941201Notes

Reaction equation

HRID 1941201 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:25]=[CH:26][C:27]=1[O:28][CH2:29][O:30][CH3:31])/[CH:6]=[CH:7]/[C:8]1[NH:16][C:15]2[C:14](=[O:17])[N:13]([CH2:18][CH2:19][CH3:20])[C:12](=[O:21])[N:11]([CH2:22][CH2:23][CH3:24])[C:10]=2[N:9]=1.[C:32](=O)([O-])[O-].[K+].[K+].CI.O>CN(C)C=O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:25]=[CH:26][C:27]=1[O:28][CH2:29][O:30][CH3:31])/[CH:6]=[CH:7]/[C:8]1[N:16]([CH3:32])[C:15]2[C:14](=[O:17])[N:13]([CH2:18][CH2:19][CH3:20])[C:12](=[O:21])[N:11]([CH2:22][CH2:23][CH3:24])[C:10]=2[N:9]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 21460354HCID 21460354, compound

Product 1

HCID 21460366HCID 21460366, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

Compound c (4.5 g, 10.5 mmol) obtained in Reference Example 3 was dissolved in 90 ml of dimethylformamide, and potassium carbonate (3.63 g, 26.26 mmol) and methyl iodide (1.31 ml, 21.04 mmol) were added thereto, followed by stirring at 50° C. for 1 hour. After cooling, water was added to the reaction mixture, and the resulting precipitate was collected by filtration. The obtained crude product was recrystallized from hexane/ethyl acetate to give 3.66 g (79% yield) of Compound d as pale yellow crystals.

Workup

  1. temperatureAfter cooling
  2. filtrationthe resulting precipitate was collected by filtration
  3. customThe obtained crude product
  4. customwas recrystallized from hexane/ethyl acetate

Sources & evidence

ORD record
ord-6c6a20d7f62e4864b9b7db250c2e8900
Source dataset
uspto-grants-1997_12
Patent number
US05703085

Reaction notes

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