Dimethylformamide → HCID 15239538, compound

HRID 1609449Notes

Reaction equation

HRID 1609449 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[N:6]=[C:5]([O:11][C:12]2[CH:26]=[CH:25][CH:24]=[C:23](OS(C(F)(F)F)(=O)=O)[C:13]=2[C:14]([O:16][CH2:17][CH2:18][Si:19]([CH3:22])([CH3:21])[CH3:20])=[O:15])[N:4]=1.CN(C=O)C.[CH:40]#[C:41][CH2:42][CH2:43][CH3:44]>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C(N(CC)CC)C>[CH3:10][O:9][C:7]1[CH:8]=[C:3]([O:2][CH3:1])[N:4]=[C:5]([O:11][C:12]2[CH:26]=[CH:25][CH:24]=[C:23]([C:40]#[C:41][CH2:42][CH2:43][CH3:44])[C:13]=2[C:14]([O:16][CH2:17][CH2:18][Si:19]([CH3:20])([CH3:21])[CH3:22])=[O:15])[N:6]=1

Participants

6

Reactant 3

HCID 6228DimethylformamideHCID 123091-PentyneHCID 15239536HCID 15239536, compound

Product 1

HCID 15239538HCID 15239538, compoundYield 62.8%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 8471TriethylamineSolvent

Procedure

In a 100 ml flask equipped with a thermometer, a cooling tube and a nitrogensintroducing tube, there were charged 2-trimethylsilylethyl 2-[(4,6-dimethoxypyrimidin-2-yl)oxy]-6-trifluoromethylsulfonyloxybenzoate (4.72 g, 9.0 mmol), bis(triphenylphosphine)palladium dichloride (300 mg, 0.4 mmol), DMF (30 ml) and triethylamine (5 ml), and the resultant mixture was stirred at room temperature for 1 hour under nitrogen stream. Thereafter, 1-pentyne (2.0 g, 29.40 mmol) was added to the resultant mixture, and the mixture was reacted at 80°-90° C. for 3 hours. After cooling, the mixture was poured into an ice water, and was extracted with ethyl acetate. The organic layer thus obtained was washed with water and a saturated salt water, dried with anhydrous sodium sulfate and concentrated. The residue thus obtained was then purified by silica gel column chromatography to obtain 2.50 g (yield: 62.8%) of the aimed product (red-brown transparent viscous liquid).

Workup

  1. customIn a 100 ml flask equipped with a thermometer, a cooling tube and a nitrogensintroducing tube, there
  2. customthe mixture was reacted at 80°-90° C. for 3 hours
  3. temperatureAfter cooling
  4. extractionwas extracted with ethyl acetate
  5. customThe organic layer thus obtained
  6. washwas washed with water
  7. dry with materiala saturated salt water, dried with anhydrous sodium sulfate
  8. concentrationconcentrated
  9. customThe residue thus obtained
  10. customwas then purified by silica gel column chromatography

Sources & evidence

ORD record
ord-7137c286cf714b1ba561fdaecb8b2f9d
Source dataset
uspto-grants-1995_03
Patent number
US05401711

Reaction notes

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