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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 70099Generated: October 26, 2026

Sodium Hydroxide → (2S,4R)-1-{2-[4-(4-chloro-phenyl)-piperazin-1-yl]-5-oxo-6,7-dihydro-5H-5lambda4-thieno[3,2-d]pyrimidin-4-yl}-4-hydroxy-pyrrolidine-2-carboxylic acid

https://huagongshe.com/reaction/70099

Reaction equation

Participants

RoleNameHCIDCharge
ReactantSodium HydroxideHCID 14798—
ReactantMETHYL (2S,4R)-1-{2-[4-(4-CHLORO-PHENYL)-PIPERAZIN-1-YL]-5-OXO-6,7-DIHYDRO-5H-5lambda4-THIENO [3,2-D]PYRIMIDIN-4-YL}-4-HYDROXY-PYRROLIDINE-2-CARBOXYLATEHCID 59708424—
SolventMethanolHCID 887—
Product(2S,4R)-1-{2-[4-(4-chloro-phenyl)-piperazin-1-yl]-5-oxo-6,7-dihydro-5H-5lambda4-thieno[3,2-d]pyrimidin-4-yl}-4-hydroxy-pyrrolidine-2-carboxylic acidHCID 59708417102.9%

Reaction Steps

1.12 g methyl (2S,4R)-1-{2-[4-(4-chloro-phenyl)-piperazin-1-yl]-5-oxo-6,7-dihydro-5H-5λ4-thieno[3,2-d]pyrimidin-4-yl}-4-hydroxy-pyrrolidine-2-carboxylate as a mixture of diastereomers (cf Example 125) and 11.38 ml of 1 molar sodium hydroxide solution are placed in 10 ml of methanol, then refluxed for 4 hours with stirring. The resulting suspension is evaporated down, the residue is cooled and acidified with 2 molar hydrochloric acid and the suspension is evaporated down again. The product is purified by preparative HPLC (method A). 1.12 g of the product are obtained as a powder.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08822474B2
Source datasetuspto-grants-2014_09
ORD IDord-60928d34106840ce8ad051abfa060522
Source noteuspto-grants-2014_09