HuagongsheHuagongshe Chemistry Print Report · For research reference only
Dimethylformamide → 1-(4-methoxybenzyl)-3-methyl-4-(5-nitropyrimidin-2-yloxy)-1H-pyrazolo[3,4-b]pyridine
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Dimethylformamide | HCID 6228 | — |
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | 2-Chloro-5-nitropyrimidine | HCID 82544 | — |
| Reactant | HCID 178490909 | HCID 178490909 | — |
| Solvent | Ethyl acetate hexane | HCID 21226206 | — |
| Product | 1-(4-methoxybenzyl)-3-methyl-4-(5-nitropyrimidin-2-yloxy)-1H-pyrazolo[3,4-b]pyridine | HCID 68513917 | 30.2% |
Reaction Steps
A 100 mL flask was charged with 1-(4-methoxybenzyl)-3-methyl-1H-pyrazolo[3,4-b]pyridin-4-ol (1.00 g, 3.71 mmol obtained from Example 5, step B), 2-chloro-5-nitropyrimidine (0.592 g, 3.71 mmol), cesium carbonate (1.21 g, 3.71 mmol) and DMF (20 mL). The solution was allowed to stir overnight at room temperature for 16.5 hours. The crude product was isolated by filtration and flash chromatography (EtOAc/Hexane 1:2) to afford 0.44 g (29%) of the desired product. LRMS M+1 (393.0) observed.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07723330B2 |
| Source dataset | uspto-grants-2010_05 |
| ORD ID | ord-bf8f3eafa732493ea212eb172d00df1c |
| Source note | uspto-grants-2010_05 |