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Methyl iodide → HCID 15292077, compound

HRID 1757582
Notes
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Reaction equation

HRID 1757582 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 3

HCID 6328Methyl iodideHCID 54167973HCID 54167973, compoundHCID 178418339Butyllithium

Product 1

HCID 15292077HCID 15292077, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent
HCID 8028
Tetrahydrofuran
Solvent

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 mmole). The reaction mixture was allowed to warm to ambient temperature then diluted with water and diethyl ether. Theether 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. customTheether layer was separated
  4. washwashed with ammonium chloride solution
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-d3e2575637f24281b89a996b72f6d194
Source dataset
uspto-grants-1995_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05446153

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes