Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Methyl iodide | HCID 6328 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | HCID 66632564 | HCID 66632564 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 66632686 | HCID 66632686 | 50.9% |
Reaction Steps
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+).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08802712B2 |
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| Source dataset | uspto-grants-2014_08 |
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| ORD ID | ord-3d3131cb9f83492a88fd226a01a793fd |
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| Source note | uspto-grants-2014_08 |
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