Water → HCID 10602221, compound

HRID 742331Notes

Reaction equation

HRID 742331 reaction equation
[H-].[Na+].[CH3:3][C:4]1[N:9]=[C:8]2[N:10]([CH2:15][C:16]3[CH:21]=[CH:20][C:19]([CH:22]([C:34]4[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=4)[CH:23]([C:29]([O:31][CH2:32][CH3:33])=[O:30])[C:24]([O:26][CH2:27][CH3:28])=[O:25])=[CH:18][CH:17]=3)[C:11]([CH2:13][CH3:14])=[N:12][C:7]2=[C:6]([CH3:40])[CH:5]=1.[CH3:41]I.O>CN(C)C=O>[CH3:3][C:4]1[N:9]=[C:8]2[N:10]([CH2:15][C:16]3[CH:17]=[CH:18][C:19]([CH:22]([C:34]4[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=4)[C:23]([C:29]([O:31][CH2:32][CH3:33])=[O:30])([C:24]([O:26][CH2:27][CH3:28])=[O:25])[CH3:41])=[CH:20][CH:21]=3)[C:11]([CH2:13][CH3:14])=[N:12][C:7]2=[C:6]([CH3:40])[CH:5]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 10529792HCID 10529792, compound

Product 1

HCID 10602221HCID 10602221, compoundYield 76.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a suspension of 55% sodium hydride in 103 mL of dimethylformamide, cooled with an ice bath, was added dropwise 13 g (25.3 mmol) of the compound obtained in example 59 dissolved in 51 mL of dimethylformamide, followed by 4.6 mL (75.9 mmol) of methyl iodide. After the addition was complete, the reaction mixture was stirred at room temperature overnight. Then, water was added and the solvent was removed. The residue was taken up in ethyl acetate and washed with brine. The organic phase was dried and the solvent was removed to yield 13 g of a crude product. This was chromatographed on silica gel (ethyl acetate-hexane mixtures of increasing polarity) to afford 10.2 g of the title compound of the example (yield: 76%).

Workup

  1. temperaturecooled with an ice bath
  2. additionAfter the addition
  3. customthe solvent was removed
  4. washwashed with brine
  5. customThe organic phase was dried
  6. customthe solvent was removed
  7. customto yield 13 g of a crude product
  8. customThis was chromatographed on silica gel (ethyl acetate-hexane mixtures of increasing polarity)

Sources & evidence

ORD record
ord-941f71aa9e8e4dfe8500bdf78d1d1917
Source dataset
uspto-grants-1996_09
Patent number
US05554624

Reaction notes

Loading…