Dimethylformamide → HCID 54193330, compound

HRID 1609447Notes

Reaction equation

HRID 1609447 reaction equation
[CH:1]([C:4]1[CH:5]=[CH:6][CH:7]=[C:8]([OH:19])[C:9]=1[C:10]([O:12][CH2:13][CH2:14][Si:15]([CH3:18])([CH3:17])[CH3:16])=[O:11])=[CH:2][CH3:3].[CH3:20][O:21][C:22]1[CH:27]=[C:26]([O:28][CH3:29])[N:25]=[C:24](S(C)(=O)=O)[N:23]=1.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>C(OCC)(=O)C>[CH3:20][O:21][C:22]1[CH:27]=[C:26]([O:28][CH3:29])[N:25]=[C:24]([O:19][C:8]2[CH:7]=[CH:6][CH:5]=[C:4]([CH:1]=[CH:2][CH3:3])[C:9]=2[C:10]([O:12][CH2:13][CH2:14][Si:15]([CH3:16])([CH3:18])[CH3:17])=[O:11])[N:23]=1

Participants

6

Reactant 4

HCID 6228Dimethylformamide3×HCID 11430Potassium CarbonateHCID 8383634,6-Dimethoxy-2-(methylsulfonyl)pyrimidineHCID 54067263HCID 54067263, compound

Product 1

HCID 54193330HCID 54193330, compoundYield 47.6%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

In a 50 ml round bottom-flask, there were charged 2-trimethylsilylethyl 6-(1-propenyl)salicylate (3.1 g, 11.0 mmol), 4,6-dimethoxy-2-methylsulfonylpyrimidine (2.4 g, 11.0 mmol), potassium carbonate (1.8 g, 13.0 mmol) and 10 ml of N,N-dimethylformamide (hereinafter referred to as "DMF"), and the resultant mixture was reacted for 1 hour at 80° C. After cooling the reaction mixture, DMF was distilled off under reduced pressure, and the residue thus obtained was dissolved in ethyl acetate, washed with water and a saturated salt water, dried with anhydrous sodium sulfate and concentrated. The resultant residue was purified by silica gel column chromatography to obtain 2.0 g (yield: 47.6%) of the aimed product (colorless transparent viscous liquid).

Workup

  1. customwas reacted for 1 hour at 80° C
  2. distillationwas distilled off under reduced pressure
  3. customthe residue thus obtained
  4. washwashed with water
  5. dry with materiala saturated salt water, dried with anhydrous sodium sulfate
  6. concentrationconcentrated
  7. customThe resultant residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-4b6e02625d9b462ba9e403305bfb4bc9
Source dataset
uspto-grants-1995_03
Patent number
US05401711

Reaction notes

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