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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2098704Generated: November 1, 2026

Sodium hydride → 3-[(2-Chloro-4-morpholin-4-yl-thieno[3,2-d]pyrimidin-6-ylmethyl)-methanesulfonyl-amino]-pyrrolidine-1-carboxylic acid tert-butyl ester

https://huagongshe.com/reaction/2098704

Reaction equation

Participants

RoleNameHCIDCharge
ReactantSodium hydrideHCID 24758—
Reactant4-(6-(Bromomethyl)-2-chlorothieno[3,2-d]pyrimidin-4-yl)morpholineHCID 46180726—
Reactanttert-Butyl 3-methanesulfonamidopyrrolidine-1-carboxylateHCID 67189774—
SolventDimethylformamideHCID 6228—
Product3-[(2-Chloro-4-morpholin-4-yl-thieno[3,2-d]pyrimidin-6-ylmethyl)-methanesulfonyl-amino]-pyrrolidine-1-carboxylic acid tert-butyl esterHCID 8661840748.4%

Reaction Steps

To a solution of 3-Methanesulfonylamino-pyrrolidine-1-carboxylic acid tert-butyl ester (0.47 g) in DMF (5 mL) was added NaH (63 mg). The mixture was stirred for 40 min. then a solution of 6-bromomethyl-2-chloro-4-morpholin-4-yl-thieno[3,2-d]pyrimidine (0.52 g) in DMF (5 mL) was added via cannular. The resulting mixture was stirred at R.T. for 5 h. An aqueous work-up followed by purification on silica gave 3-[(2-chloro-4-morpholin-4-yl-thieno[3,2-d]pyrimidin-6-ylmethyl)-methanesulfonyl-amino]-pyrrolidine-1-carboxylic acid tert-butyl ester (384 mg).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08450315B2
Source datasetuspto-grants-2013_05
ORD IDord-c522cd548e724f678fd1febf17c71610
Source noteuspto-grants-2013_05