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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 237397Generated: October 25, 2026

Sodium hydride → 2-Amino-4-(benzo[1,3]dioxol-5-yl-cyano-methyl)-thieno[2,3-d]pyrimidine-6-carboxylic acid ethyl ester

https://huagongshe.com/reaction/237397

Reaction equation

Participants

RoleNameHCIDCharge
ReactantSodium hydrideHCID 24758—
Reactant3,4-(Methylenedioxy)phenylacetonitrileHCID 78178—
ReactantEthyl 2-amino-4-chlorothieno(2,3-d)pyrimidine-6-carboxylateHCID 16096301—
SolventDimethylformamideHCID 6228—
SolventSodium chloride; waterHCID 57417360—
Product2-Amino-4-(benzo[1,3]dioxol-5-yl-cyano-methyl)-thieno[2,3-d]pyrimidine-6-carboxylic acid ethyl esterHCID 59519339—

Reaction Steps

To a solution of 2-amino-4-chloro-thieno[2,3-d]pyrimidine-6-carboxylic acid ethyl ester (1 equiv.) and benzo[1,3]dioxol-5-yl-acetonitrile (1 mole eq.) in DMF at room temperature, sodium hydride (1.1 mole eq., 60% in mineral oil) was added. The mixture was stirred at this temperature overnight under argon. After that, it was diluted with brine and extracted with ethyl acetate. The combined organic portions were washed with brine and water and dried with sodium sulphate. After filtration and evaporation of the solvent, brown solids were obtained which were purified either by preparative TLC or preparative HPLC.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08642594B2
Source datasetuspto-grants-2014_02
ORD IDord-531272634c83410985e09d780a325f76
Source noteuspto-grants-2014_02