HuagongsheHuagongshe Chemistry Print Report · For research reference only
Water → 2-[(2-chloro-6-hydroxyphenyl)methylsulfanyl]-6-methyl-1H-pyrimidin-4-one
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Sodium Sulfate | HCID 24436 | — |
| Reactant | Boron tribromide | HCID 25134 | — |
| Reactant | HCID 178490246 | HCID 178490246 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | 2-[(2-chloro-6-hydroxyphenyl)methylsulfanyl]-6-methyl-1H-pyrimidin-4-one | HCID 178429512 | 95% |
Reaction Steps
In a 250 mL round bottom flask, 2-{[(2-chloro-6-methoxyphenyl)methyl]sulfanyl}-6-methylpyrimidin-4-ol (200 mg, 0.67 mmol) was dissolved in DCM (10 mL). BBr3 (1.42 mL, 1.42 mmol) was added dropwise. The resulting mixture was stirred at room temperature overnight. Water (5 mL) was added, followed by Na2SO4 (20 g) and DCM (100 mL) after 5 minutes. The solution was filtered and evaporated. The crude product was purified by column chromatography to provide the title compound as a white solid (180 mg, 95% yield); 1H NMR (400 MHz, DMSO-d6): δ 2.06 (s, 3H), 4.48 (s, 2H), 6.02 (br, 1H), 6.83 (d, 1H), 6.93 (d, 1H), 7.15 (t, 1H), 10.44 (br, 1H); M+ 283.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09040538B2 |
| Source dataset | uspto-grants-2015_05 |
| ORD ID | ord-8d9c54eac36a44e6ba5efa76362b5597 |
| Source note | uspto-grants-2015_05 |