Methyl iodide → HCID 10268853, compound

HRID 1451747Notes

Reaction equation

HRID 1451747 reaction equation
[H-].[Na+].O.[NH2:4][C:5]1[C:14]2[N:15]=[C:16]([CH:22]([CH2:24][CH2:25][CH2:26][CH3:27])[OH:23])[N:17]([CH2:18][CH:19]([CH3:21])[CH3:20])[C:13]=2[C:12]2[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=2[N:6]=1.N[C:29]1C2N=C(C(CCCC)O)N(CC(C)C)C=2C2C=CC=CC=2N=1.CI>>[CH3:29][O:23][CH:22]([C:16]1[N:17]([CH2:18][CH:19]([CH3:20])[CH3:21])[C:13]2[C:12]3[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=3[N:6]=[C:5]([NH2:4])[C:14]=2[N:15]=1)[CH2:24][CH2:25][CH2:26][CH3:27]

Participants

4

Reactant 3

HCID 6328Methyl iodide2×HCID 24758Sodium hydride2×HCID 69878358HCID 69878358, compound

Product 1

HCID 10268853HCID 10268853, compoundYield 16%

Procedure

Sodium hydride (0.32 g; 10.1 mmol) was added to a suspension of 4-amino-α-butyl-1-(2-methylpropyl)-1H-imidazo[4,5-c]quinoline-2-methanol (3 g; 9.2 mmol, Example 60) and the resulting mixture was stirred for about 2 hours. Methyl iodide (0.82 mL; 13.8 mmol) was added to the mixture and stirring was continued overnight. Thin layer chromatography indicated that the reaction was incomplete so sodium hydride (0.25 g) was added followed two hours later by methyl iodide (1 mL). The reaction was stirred for several additional hours then quenched with water and diluted with ethyl acetate. The organic layer was separated, washed with water, dried over magnesium sulfate and concentrated under vacuum to provide an oil. The oil was purified by silica gel chromatography (1-3% methanol in methylene chloride as eluent) to provide 0.5 g of a solid, m.p. 125°-128° C. Analysis: Calculated: C, 70.55; H, 8.3; % N, 16.5; Found: C, 70.2; H, 8.3; N, 16.0.

Workup

  1. stirringstirring
  2. waitwas continued overnight
  3. additionwas added
  4. stirringThe reaction was stirred for several additional hours
  5. customthen quenched with water
  6. additiondiluted with ethyl acetate
  7. customThe organic layer was separated
  8. washwashed with water
  9. dry with materialdried over magnesium sulfate
  10. concentrationconcentrated under vacuum
  11. customto provide an oil
  12. customThe oil was purified by silica gel chromatography (1-3% methanol in methylene chloride as eluent)

Sources & evidence

ORD record
ord-8f34725a6e0a4776ab8e022db9203d8e
Source dataset
uspto-grants-1997_02
Patent number
US05605899

Reaction notes

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