Methyl iodide → HCID 86635441, compound

HRID 2353435Notes

Reaction equation

HRID 2353435 reaction equation
[F:1][C:2]([F:19])([F:18])[C:3]1[NH:7][C:6]2[CH2:8][N:9]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:10][C:5]=2[N:4]=1.[CH3:20][Si]([N-][Si](C)(C)C)(C)C.[K+].CI>O1CCCC1>[CH3:20][N:4]1[CH:5]2[CH2:10][N:9]([C:11]([O:13][C:14]([CH3:15])([CH3:16])[CH3:17])=[O:12])[CH2:8][CH:6]2[N:7]=[C:3]1[C:2]([F:1])([F:18])[F:19]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 3251421Potassium bis(trimethylsilyl)amideHCID 68717761HCID 68717761, compound

Product 1

HCID 86635441HCID 86635441, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of tert-butyl 2-(trifluoromethyl)-4,6-dihydropyrrolo[3,4-d]imidazole-5(1H)-carboxylate (90 mg) in tetrahydrofuran (3 mL) at −20° C. was added potassium bis(trimethylsilyl)amide solution (0.714 mL 0.5M in toluene). The mixture was stirred at −20° C. for 30 min at which point methyl iodide (0.04 mL) was added and the reaction slowly was warmed to ambient temperature over 1 h. The reaction mixture was quenched with saturated aqueous sodium bicarbonate solution (5 mL). The phases were separated and the aqueous phase extracted with dichloromethane (3×10 mL). The combined organic phases were dried over anhydrous sodium sulfate, filtered, evaporated in vacuo and the resulting product used without further purification. LC/MS 292.2 (M+1).

Workup

  1. additionwas added
  2. customthe reaction
  3. customThe reaction mixture was quenched with saturated aqueous sodium bicarbonate solution (5 mL)
  4. customThe phases were separated
  5. extractionthe aqueous phase extracted with dichloromethane (3×10 mL)
  6. dry with materialThe combined organic phases were dried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. customevaporated in vacuo
  9. customthe resulting product used without further purification

Sources & evidence

ORD record
ord-3c2cef1f2a4e482387fb8d7204d057ac
Source dataset
uspto-grants-2010_07
Patent number
US07750034B2

Reaction notes

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