Methyl iodide → HCID 15292077, compound

HRID 263726Notes

Reaction equation

HRID 263726 reaction equation
[CH2:1]([Li])CCC.[CH3:6][C:7]1[N:8]([CH2:33][CH:34]([CH3:36])[CH3:35])[C:9]2[C:14]([CH3:15])=[C:13]([CH3:16])[N:12]=[C:11]([N:17]([CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[C:10]=2[N:32]=1.CI>O1CCCC1.O.C(OCC)C>[CH2:6]([C:7]1[N:8]([CH2:33][CH:34]([CH3:36])[CH3:35])[C:9]2[C:14]([CH3:15])=[C:13]([CH3:16])[N:12]=[C:11]([N:17]([CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH2:25][C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=3)[C:10]=2[N:32]=1)[CH3:1]

Participants

7

Reactant 3

HCID 6328Methyl iodideHCID 54167973HCID 54167973, compoundHCID 178418339Butyllithium

Product 1

HCID 15292077HCID 15292077, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-10 °C

Procedure

Butyllithium (0.5 mL of 2.5M in hexanes) was added to a cooled (-78° C.) solution of 2,6,7-trimethyl-1-(2-methylpropyl)-N4,N4 -bis(phenylmethyl)-1H-imidazo[4,5-c]pyridin-4-amine (0.5 g, 1.2 mmole) in tetrahydrofuran (30 mL). The reaction mixture was allowed to warm to -10° C. then it was cooled to -78° C. and combined with methyl iodide (0.23 mL, 3.6 mole). The reaction mixture was allowed to warm to ambient temperature then diluted with water and diethyl ether. The ether layer was separated, washed with ammonium chloride solution, dried over magnesium sulfate and then concentrated to provide 0.5 g of the desired product.

Workup

  1. temperatureit was cooled to -78° C.
  2. temperatureto warm to ambient temperature
  3. customThe ether layer was separated
  4. washwashed with ammonium chloride solution
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-805e33f180a94b3dbdffa3f4d5a4497f
Source dataset
uspto-grants-1997_07
Patent number
US05644063

Reaction notes

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