Methyl iodide → HCID 89497909, compound

HRID 1430324Notes

Reaction equation

HRID 1430324 reaction equation
[CH:1]1([CH:7]([N:11]2[CH:15]=[CH:14][CH:13]=[N:12]2)[CH2:8][CH2:9][OH:10])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[H-].[Na+].[CH3:18]I>O1CCCC1>[CH:1]1([CH:7]([N:11]2[CH:15]=[CH:14][CH:13]=[N:12]2)[CH2:8][CH2:9][O:10][CH3:18])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 89498330HCID 89498330, compound

Product 1

HCID 89497909HCID 89497909, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of EXAMPLE 184A (0.23 g) in dry tetrahydrofuran (5 mL) was added sodium hydride (0.166 g) at 0° C. The reaction mixture was stirred for 60 minutes when methyl iodide (0.259 mL) was added and stirring was continued for 4 hours at room temperature. The reaction mixture was quenched with ammonium chloride solution (5 mL), and extracted with ethyl acetate. The organic layer was dried over magnesium sulfate, filtered and concentrated. The crude material was purified by flash chromatography on silica gel, and was eluted with 10-60% ethyl acetate/hexanes.

Workup

  1. additionwas added
  2. customThe reaction mixture was quenched with ammonium chloride solution (5 mL)
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude material was purified by flash chromatography on silica gel
  8. washwas eluted with 10-60% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-e6a6939dad8148cdb0110e1a1e56662b
Source dataset
uspto-grants-2015_01
Patent number
US08940737B2

Reaction notes

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