HuagongsheHuagongshe Chemistry Print Report · For research reference only
Pyridine → 6-bromo-4-(4-chlorobenzyl)-2-(2-(hydroxymethyl)phenyl)-1,2,4-triazine-3,5(2H,4H)-dione
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Pyridine | HCID 1049 | — |
| Reactant | 2-(Hydroxymethyl)phenylboronic Acid | HCID 4374262 | — |
| Reactant | 4-(4-chlorobenzyl)-6-bromo-1,2,4-triazine-3,5(2H,4H)-dione | HCID 68703354 | — |
| Catalyst | Cupric acetate | HCID 8895 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | 6-bromo-4-(4-chlorobenzyl)-2-(2-(hydroxymethyl)phenyl)-1,2,4-triazine-3,5(2H,4H)-dione | HCID 68702525 | 62% |
Reaction Steps
According to Scheme 2 Step 3: To a solution of 6-bromo-4-(4-chlorobenzyl)-1,2,4-triazine-3,5(2H,4H)-dione (0.400 g, 1.3 mmol) in DMF (8 mL) were added 2-(hydroxymethyl)phenylboronic acid (0.29 g, 1.9 mmol), copper(II) acetate (0.23 g, 1.3 mmol) and pyridine (0.20 g, 2.5 mmol) and the mixture was left stiffing overnight at 60° C. The reaction mixture was quenched with a saturated sodium bicarbonate solution. The precipitate formed was filtered, washed first with water and then with diethyl ether. 330 mg (Yield=62%) of 6-bromo-4-(4-chlorobenzyl)-2-(2-(hydroxymethyl)phenyl)-1,2,4-triazine-3,5(2H,4H)-dione were recovered. The product was pure enough to be used without any purification.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08779129B2 |
| Source dataset | uspto-grants-2014_07 |
| ORD ID | ord-9495d5db4bda4c8a848930fd8860b9a3 |
| Source note | uspto-grants-2014_07 |