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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 237398Generated: October 25, 2026

Dimethylacetamide → 2-Amino-4-cyano-thieno[2,3-d]pyrimidine-6-carboxylic acid ethyl ester

https://huagongshe.com/reaction/237398

Reaction equation

Participants

RoleNameHCIDCharge
ReactantDimethylacetamideHCID 31374—
ReactantEthyl 2-amino-4-chlorothieno(2,3-d)pyrimidine-6-carboxylateHCID 16096301—
CatalystZinc cyanide (Zn(CN)2)HCID 11186—
CatalystZincHCID 23994—
CatalystFerrocene-1,1'-bis-(diphenylphosphine)HCID 635956—
CatalystBis(dibenzylideneacetone)palladiumHCID 9811564—
Product2-Amino-4-cyano-thieno[2,3-d]pyrimidine-6-carboxylic acid ethyl esterHCID 59519342—

Reaction Conditions

Temperature120 °C

Reaction Steps

2-Amino-4-chloro-thieno[2,3-d]pyrimidine-6-carboxylic acid ethyl ester (1 equiv.), Zn(CN)2 (0.6 equiv.), Zn dust (0.12 equiv.), Pd2(dba)3 (0.02 mole eq.) and 1,1′-bis(diphenylphosphino)ferrocene (0.04 equiv.) were mixed in DMA and the mixture was stirred under argon at 120° C. for 24 hours. The resulting suspension was filtered through a short Celite column, the filtrate was diluted with brine and extracted with ethyl acetate. The organic layer was then washed with brine, water and dried over sodium sulphate. After evaporation of the solvent, the crude oil was purified by preparative TLC.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08642594B2
Source datasetuspto-grants-2014_02
ORD IDord-8ac7a9a78b8c4221be440008c345952c
Source noteuspto-grants-2014_02