HuagongsheHuagongshe Chemistry Print Report · For research reference only
Thioglycolic Acid → 2-(ethylsulfanyl)-3-[4-(2,2,2-trifluoroethoxy)phenyl]-3H-pyrimido[5,4-b][1,4]thiazine-4,7(6H,8H)-dione
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Thioglycolic Acid | HCID 1133 | — |
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | 6-amino-5-bromo-2-(ethylsulfanyl)-3-[4-(2,2,2-trifluoroethoxy)phenyl]pyrimidin-4(3H)-one | HCID 86685376 | — |
| Solvent | Toluene | HCID 1140 | — |
| Product | 2-(ethylsulfanyl)-3-[4-(2,2,2-trifluoroethoxy)phenyl]-3H-pyrimido[5,4-b][1,4]thiazine-4,7(6H,8H)-dione | HCID 86685375 | — |
Reaction Steps
A solution of 6-amino-5-bromo-2-(ethylsulfanyl)-3-[4-(2,2,2-trifluoroethoxy)phenyl]pyrimidin-4(3H)-one (0.1 g) and mercaptoacetic acid (0.168 mL) in toluene (2 mL) was stirred at 170° C. for 2 hr under microwave irradiation. To the reaction mixture was added saturated aqueous sodium hydrogen carbonate solution, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (0.04 g).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09023858B2 |
| Source dataset | uspto-grants-2015_05 |
| ORD ID | ord-431779a2f296488683e6be31d8997181 |
| Source note | uspto-grants-2015_05 |