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Methyl iodide → HCID 15292077, compound

HRID 2396751
Notes
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Reaction equation

HRID 2396751 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. 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-3e7b42e103864ec2ac9ccf46e4f31989
Source dataset
uspto-grants-1996_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05494916

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes