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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 928620Generated: October 25, 2026

Triethylamine → 1-[4-[3-Hydroxy-8-azabicyclo[3.2.1]octan-8-yl]-5-phenyl-thieno[2,3-d]pyrimidin-2-yl]pyrrolidine-3-carboxamide

https://huagongshe.com/reaction/928620

Reaction equation

Participants

RoleNameHCIDCharge
ReactantTriethylamineHCID 8471—
ReactantPyrrolidine-3-carboxamide hydrochlorideHCID 50988639—
Reactant8-(2-Chloro-5-phenyl-thieno[2,3-d]pyrimidin-4-yl)-8-azabicyclo[3.2.1]octan-3-olHCID 89579588—
SolventAcetonitrileHCID 6342—
Product1-[4-[3-Hydroxy-8-azabicyclo[3.2.1]octan-8-yl]-5-phenyl-thieno[2,3-d]pyrimidin-2-yl]pyrrolidine-3-carboxamideHCID 8957950081.6%

Reaction Conditions

Temperature150 °C

Reaction Steps

8-(2-Chloro-5-phenyl-thieno[2,3-d]pyrimidin-4-yl)-8-azabicyclo[3.2.1]octan-3-ol (44 mg, 0.12 mmol) was suspended in acetonitrile (3 mL). Pyrrolidine-3-carboxamide hydrochloride (36 mg, 0.24 mmol) and triethylamine (0.067 mL, 0.47 mmol) were added and the mixture was heated to 150° C. for 30 min in a microwave (twice). Further batches of pyrrolidine-3-carboxamide hydrochloride (36 mg, 0.24 mmol) and triethylamine (0.067 mL, 0.47 mmol) were added and the mixtures were heated to 150° C. for 30 min in a microwave. The solvent was evaporated and the residue was purified by LCUV (acidic method 1) to give the target compound as a white solid (44 mg). m/z [M+H]+450.1. Retention time 3.75 min (LCMS method+ve 6 min).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09290511B2
Source datasetuspto-grants-2016_03
ORD IDord-689dfd6514304ac09fe436377edaa063
Source noteuspto-grants-2016_03