Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Potassium Iodide | HCID 4875 | — |
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | HCID 86677638 | HCID 86677638 | — |
| Reactant | HCID 178508725 | HCID 178508725 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 71510766 | HCID 71510766 | 47.2% |
Reaction Steps
To a mixture of 3-iodo-1H-pyrazolo[3,4-d]pyrimidin-4-amine (from CNH Technologies, 120 mg, 0.46 mmol), cesium carbonate (200 mg, 0.62 mmol) and potassium iodide (7.0 mg, 0.042 mmol) in N,N-dimethylformamide (1 mL) was added 5-[3-chloro-5-(1-chloroethyl)-6-ethoxy-2-methylphenyl]-N,N-dimethylpyridine-2-carboxamide (160 mg, 0.42 mmol, from Example 14, step 4) and the mixture was stirred at 140° C. for 1 hour. The reaction mixture was diluted with water, extracted with ether. The combined organic layers were dried over MgSO4, concentrated and purified on silica gel (eluting with 0 to 10% MeOH in dichloromethane) to give the desired product (0.12 g, 47%). The product was isolated as a racemic mixture. LCMS calculated for C24H26ClIN7O2 (M+H)+: m/z=606.1; Found: 606.0.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09199982B2 |
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| Source dataset | uspto-grants-2015_12 |
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| ORD ID | ord-96f87e49017c40078583161a901dd548 |
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| Source note | uspto-grants-2015_12 |
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