Ethylene Oxide → HCID 18995664, compound

HRID 374981Notes

Reaction equation

HRID 374981 reaction equation
[C:1]1([CH2:7][N:8]([CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:9]2[C:18]3[N:19]=[C:20]([CH3:26])[N:21]([CH2:22][O:23][CH2:24][CH3:25])[C:17]=3[C:16]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[N:10]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([Li])CCC.[CH2:39]1[O:41][CH2:40]1>O1CCCC1>[C:28]1([CH2:27][N:8]([CH2:7][C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[C:9]2[C:18]3[N:19]=[C:20]([CH2:26][CH2:39][CH2:40][OH:41])[N:21]([CH2:22][O:23][CH2:24][CH3:25])[C:17]=3[C:16]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[N:10]=2)[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

5

Reactant 3

HCID 6354Ethylene Oxide2×HCID 18995659HCID 18995659, compoundHCID 178418339Butyllithium

Product 1

HCID 18995664HCID 18995664, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of N,N-bis(phenylmethyl)-1-ethoxymethyl-2-methyl-1H-imidazo[4,5-c]quinolin-4-amine (1.7 g, 3.9 mmole, Example 1 Part E) in tetrahydrofuran (50 mL) was cooled to -78° C. Butyllithium (1.6 mL of 2.5M in hexanes, 4.1 mmole) was added dropwise and the reaction mixture was stirred for 5 minutes. Ethylene oxide was run over the surface of the reaction mixture. After 10 minutes the reaction mixture was allowed to warm to ambient temperature. The ethylene oxide addition was stopped when the reaction temperature reached 0° C. The reaction was quenched with diethyl ether and water. The ether layer was separated, dried over magnesium sulfate and then concentrated under vacuum. The resulting residue was purified by column chromatography (silica gel eluting with 5-10% ethyl acetate in methylene chloride v/v) to provide 1.4 g of N,N-bis(phenylmethyl)-2-(3-hydroxypropyl)-1-ethoxymethyl-1H-imidazo[4,5-c]quinolin-4-amine.

Workup

  1. waitAfter 10 minutes the reaction mixture was allowed
  2. customreached 0° C
  3. customThe reaction was quenched with diethyl ether and water
  4. customThe ether layer was separated
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under vacuum
  7. customThe resulting residue was purified by column chromatography (silica gel eluting with 5-10% ethyl acetate in methylene chloride v/v)

Sources & evidence

ORD record
ord-2396789f306546938d79e89da51bdf26
Source dataset
uspto-grants-1996_01
Patent number
US05482936

Reaction notes

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