HuagongsheHuagongshe Chemistry Print Report · For research reference only
Potassium Carbonate → 4-({2-[1-(2-fluorobenzyl)-1H-indazol-3-yl]-5-hydroxypyrimidin-4-yl}amino)pyridine-3-carbonitrile
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | 4-Bromopyridine-3-carbonitrile | HCID 22329522 | — |
| Reactant | 2-[1-(2-fluorobenzyl)-1H-indazol-3-yl]-5-methoxypyrimidin-4-amine | HCID 86732425 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | 4-({2-[1-(2-fluorobenzyl)-1H-indazol-3-yl]-5-hydroxypyrimidin-4-yl}amino)pyridine-3-carbonitrile | HCID 136341425 | — |
Reaction Conditions
| Temperature | 100 °C |
|---|
Reaction Steps
50 mg of 4-amino-2-[1-(2-fluorobenzyl)-1H-indazol-3-yl]pyrimidin-5-ol (1-11-1, 0.149 mmol, 1. eq.) were dissolved in 3 ml of N,N-dimethylformamide. 103 mg of potassium carbonate (0.746 mmol, 5 eq.) and 32.8 mg of 4-bromopyridine-3-carbonitrile (0.179 mmol, 1.2 eq.) were added. The reaction mixture was stirred at 100° C. bath temperature for 18 hours. After cooling at room temperature the mixture was filtered off and washed with dichloromethane. The filtrate was concentrated in vacuo. The residue was purified by preparative HPLC and preparative TLC to yield 4.21 mg (0.01 mmol, 6.1%) of the analytically pure target compound.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09265763B2 |
| Source dataset | uspto-grants-2016_02 |
| ORD ID | ord-720afc656ec243a5941f741e1c17d91a |
| Source note | uspto-grants-2016_02 |