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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1094737Generated: October 26, 2026

Sodium hydride → Methyl 5-methyl-4-oxo-3-(2-(2-oxopyrrolidin-1-yl)ethyl)-3,4-dihydrothieno[2,3-d]pyrimidine-6-carboxylate

https://huagongshe.com/reaction/1094737

Reaction equation

Participants

RoleNameHCIDCharge
ReactantSodium hydrideHCID 24758—
ReactantMethyl 5-methyl-4-oxo-3,4-dihydrothieno[2,3-d]pyrimidine-6-carboxylateHCID 725279—
Reactant2-(2-Oxopyrrolidin-1-yl)ethyl methanesulfonateHCID 44627116—
SolventDimethylformamideHCID 6228—
ProductMethyl 5-methyl-4-oxo-3-(2-(2-oxopyrrolidin-1-yl)ethyl)-3,4-dihydrothieno[2,3-d]pyrimidine-6-carboxylateHCID 5984288242.6%

Reaction Steps

To a solution of methyl 5-methyl-4-oxo-3,4-dihydrothieno[2,3-d]pyrimidine-6-carboxylate (0.8 g, 3.5 mmol) in DMF (10 ml) was added NaH (0.28 g, 7 mmol) followed by the addition of 2-(2-oxopyrrolidin-1-yl)ethyl methanesulfonate (0.7 g, 3.5 mmol). The mixture was then stirred overnight at RT. Reaction was quenched with water (10 ml) and mixture extracted with ethyl acetate. Ethyl acetate layer was separated, dried over anhydrous sodium sulfate and evaporated to yield 0.5 g of methyl 5-methyl-4-oxo-3-(2-(2-oxopyrrolidin-1-yl)ethyl)-3,4-dihydrothieno[2,3-d]pyrimidine-6-carboxylate, as an oil (yield: 42.8%).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08133998B2
Source datasetuspto-grants-2012_03
ORD IDord-5bf84413c1924dd0a07d7a93e565319b
Source noteuspto-grants-2012_03