Methyl iodide → HCID 15239541, compound

HRID 1609450Notes

Reaction equation

HRID 1609450 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:20]=[CH:19][CH:18]=[C:17]([C:21]#[C:22][CH2:23][CH2:24][CH3:25])[C:13]=2[C:14]([O-:16])=[O:15])[N:4]=1.[CH:26]([NH2+]C(C)C)(C)C.CI>O1CCCC1.CN(C=O)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:20]=[CH:19][CH:18]=[C:17]([C:21]#[C:22][CH2:23][CH2:24][CH3:25])[C:13]=2[C:14]([O:16][CH3:26])=[O:15])[N:6]=1

Participants

5

Reactant 2

HCID 6328Methyl iodideHCID 15239539HCID 15239539, compound

Product 1

HCID 15239541HCID 15239541, compoundYield 76.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

Diisopropylammonium 2-[(4,6-dimethoxypyrimidin-2-yl)oxy]-6-(1-pentynyl)benzoate (1.00 g, 2.3 mmol) was dissolved in tetrahydrofuran (20 ml)-DMF (10 ml) in a 50 ml round bottom-flask, and methyl iodide (1.4 g, 10.0 mmol) was added thereto little by little. The resultant mixture was stirred at 50° C. for 2 hours and THF-DMF was distilled off under reduced pressure. Water was added to the resultant residue, and the residue 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. To the resultant mixture, was added an appropriate amount of Florisil, and the mixture was eluted with ispropyl ether. The solvent was then distilled off under reduced pressure to obtain 0.61 g (yield: 76.3 %) of the aimed product (yellow viscous liquid).

Workup

  1. distillationTHF-DMF was distilled off under reduced pressure
  2. additionWater was added to the resultant residue
  3. extractionthe residue was extracted with ethyl acetate
  4. customThe organic layer thus obtained
  5. washwas washed with water
  6. dry with materiala saturated salt water, dried with anhydrous sodium sulfate
  7. concentrationconcentrated
  8. additionTo the resultant mixture, was added an appropriate amount of Florisil
  9. washthe mixture was eluted with ispropyl ether
  10. distillationThe solvent was then distilled off under reduced pressure

Sources & evidence

ORD record
ord-2497f83a777048f1964330c0dfb1e20d
Source dataset
uspto-grants-1995_03
Patent number
US05401711

Reaction notes

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