Methyl iodide → HCID 66632686, compound

HRID 2404245Notes

Reaction equation

HRID 2404245 reaction equation
[CH3:1][O:2][C:3]1[C:4]([O:26][CH3:27])=[CH:5][C:6]2[C:7]3[C:15]([C:16]4[CH:23]=[CH:22][C:19]([C:20]#[N:21])=[C:18]([CH2:24][OH:25])[CH:17]=4)=[N:14][NH:13][C:8]=3[CH:9]=[N:10][C:11]=2[CH:12]=1.CI.[C:30](=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH3:1][O:2][C:3]1[C:4]([O:26][CH3:27])=[CH:5][C:6]2[C:7]3[C:15]([C:16]4[CH:23]=[CH:22][C:19]([C:20]#[N:21])=[C:18]([CH2:24][OH:25])[CH:17]=4)=[N:14][N:13]([CH3:30])[C:8]=3[CH:9]=[N:10][C:11]=2[CH:12]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 66632564HCID 66632564, compound

Product 1

HCID 66632686HCID 66632686, compoundYield 50.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-(7,8-Dimethoxy-3H-pyrazolo[3,4-c]quinolin-1-yl)-2-hydroxymethylbenzonitrile (78 mg, 216 μmol) is dissolved in N,N-dimethylformamide (1.0 ml) under argon, and methyl iodide (34 μl, 541 μmol) and potassium carbonate (60 mg, 433 μmol) are subsequently added. The suspension is stirred at room temperature for 1 h. For purification, the mixture is extracted with ethyl acetate and semi-saturated sodium chloride solution. The organic phase is dried over Na2SO4, filtered with suction and evaporated to dryness in vacuo. The residue is purified by chromatography (pHPLC, solvent gradient water/1-30% by vol. of acetonitrile, 0.1% by vol. of formic acid), and the product fractions are lyophilised, giving 4-(7,8-dimethoxy-3-methyl-3H-pyrazolo[3,4-c]quinolin-1-yl)-2-hydroxymethylbenzonitrile (41 mg, 110 μmol) as a solid. MS: 375.2 (M+H+).

Workup

  1. customFor purification
  2. extractionthe mixture is extracted with ethyl acetate and semi-saturated sodium chloride solution
  3. dry with materialThe organic phase is dried over Na2SO4
  4. filtrationfiltered with suction
  5. customevaporated to dryness in vacuo
  6. customThe residue is purified by chromatography (pHPLC, solvent gradient water/1-30% by vol. of acetonitrile, 0.1% by vol. of formic acid)

Sources & evidence

ORD record
ord-3d3131cb9f83492a88fd226a01a793fd
Source dataset
uspto-grants-2014_08
Patent number
US08802712B2

Reaction notes

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