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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 240628Generated: October 25, 2026

Sodium Hydroxide → 4-[2-((R)-1-tert-Butoxycarbonyl-piperidin-3-yloxy)-4-fluoro-Phenylamino]-5-methyl-thieno[2,3-d]pyrimidine-6-carboxylic acid

https://huagongshe.com/reaction/240628

Reaction equation

Participants

RoleNameHCIDCharge
ReactantSodium HydroxideHCID 14798—
Reactant4-[2-((R)-1-tert-Butoxycarbonyl-piperidin-3-yloxy)-4-fluoro-phenylamino]-5-methyl-thieno[2,3-d]pyrimidine-6-carboxylic acid methyl esterHCID 58413127—
SolventMeOH tetrahydrofuranHCID 21899815—
Product4-[2-((R)-1-tert-Butoxycarbonyl-piperidin-3-yloxy)-4-fluoro-Phenylamino]-5-methyl-thieno[2,3-d]pyrimidine-6-carboxylic acidHCID 58413057—

Reaction Steps

A mixture of 4-[2-((R)-1-tert-Butoxycarbonyl-piperidin-3-yloxy)-4-fluoro-phenylamino]-5-methyl-thieno[2,3-d]pyrimidine-6-carboxylic acid methyl ester (1.65 g) in MeOH/THF (1:1; 20 ml) was treated with NaOH (2M; 8 ml) and heated at reflux for 10 mins. Organic solvent was removed in vacuo. HCl (2M; 8 ml) was added to pH 1 and water was added. The suspension was filtered and washed with water. The solid was suspended in EtOH and evaporated. The residue was triturated with Acetonitrile to give the desired product.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08648068B2
Source datasetuspto-grants-2014_02
ORD IDord-0cce96f0b7684110914f88a568983c6f
Source noteuspto-grants-2014_02