Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | Cyclohexane, (bromomethyl)- | HCID 137636 | — |
| Reactant | HCID 178508328 | HCID 178508328 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 46830431 | HCID 46830431 | — |
Reaction Steps
200 mg (0.691 mmol) of 2-(1H-pyrazolo[3,4-b]pyridin-3-yl)-5-(pyridin-4-yl)pyrimidine-4-amine (preparation: see WO 03/097063, Example 35A) were dissolved in 5 ml of DMF, and 248 mg (0.760 mmol) of cesium carbonate and 136 mg (0.760 mmol) of cyclohexylmethyl bromide were added. The mixture was stirred at RT overnight. Water was added, and the mixture was extracted three times with dichloromethane. The combined organic phases were washed with saturated aqueous sodium chloride solution, dried over sodium sulfate and concentrated on a rotary evaporator. The residue was fractionated by preparative HPLC (Method 5). The product-containing fractions were combined and concentrated on a rotary evaporator, and the residue was dried under high vacuum. This gave 29 mg (11% of theory) of the target compound.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08334291B2 |
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| Source dataset | uspto-grants-2012_12 |
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| ORD ID | ord-ecd5d6fb96ef4d13a6d7daad59af9cc1 |
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| Source note | uspto-grants-2012_12 |
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