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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 570716Generated: October 30, 2026

Thioglycolic Acid → 2-(ethylsulfanyl)-3-[4-(2,2,2-trifluoroethoxy)phenyl]-3H-pyrimido[5,4-b][1,4]thiazine-4,7(6H,8H)-dione

https://huagongshe.com/reaction/570716

Reaction equation

Participants

RoleNameHCIDCharge
ReactantThioglycolic AcidHCID 1133—
ReactantSodium BicarbonateHCID 516892—
Reactant6-amino-5-bromo-2-(ethylsulfanyl)-3-[4-(2,2,2-trifluoroethoxy)phenyl]pyrimidin-4(3H)-oneHCID 86685376—
SolventTolueneHCID 1140—
Product2-(ethylsulfanyl)-3-[4-(2,2,2-trifluoroethoxy)phenyl]-3H-pyrimido[5,4-b][1,4]thiazine-4,7(6H,8H)-dioneHCID 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

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09023858B2
Source datasetuspto-grants-2015_05
ORD IDord-431779a2f296488683e6be31d8997181
Source noteuspto-grants-2015_05