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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 495480Generated: October 31, 2026

Triethylamine; trifluoroacetic acid → 3-{2-Methoxy-4-[4-(quinolin-3-ylamino)-pyrimidin-2-ylamino]-phenyl}-1-pyrrolidin-1-yl-propanone

https://huagongshe.com/reaction/495480

Reaction equation

Participants

RoleNameHCIDCharge
ReactantTriethylamine; trifluoroacetic acidHCID 12210277—
Reactant(2-Chloropyrimidin-4-yl)quinolin-3-ylamineHCID 22326846—
Reactant3-(4-Amino-2-methoxy-phenyl)-1-pyrrolidin-1-yl-propan-1-oneHCID 22326858—
SolventDimethyl SulfoxideHCID 679—
Product3-{2-Methoxy-4-[4-(quinolin-3-ylamino)-pyrimidin-2-ylamino]-phenyl}-1-pyrrolidin-1-yl-propanoneHCID 69738425—

Reaction Conditions

Temperature100 °C

Reaction Steps

To a solution of (2-chloro-pyrimidin-4-yl)-quinolin-3-yl-amine (0.5 g, 1.8 mmol, 1.0 eq.) and 3-(4-amino-2-methoxy-phenyl)-1-pyrrolidin-1-yl-propan-1-one (0.47 g, 2.0 mmol, 1.1 eq. Step B) in 0.5 mL of DMSO was added a 1/1 (v/v) mixture of TFA/Et3N (337 μl, 1.8 mmol, 1.0 eq.). The reaction was heated to 100° C. and stirred for 16 h. The mixture was cooled, concentrated and purified by column chromatography (0-5% MeOH in CH2Cl2 with 1% of NH4OH (aq.)). Triturated with CH2Cl2 to provide the title compound. MS m/z=469.6 (M+H)+ Calc'd for C27H28N6O2: 468.56.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS06939874B2
Source datasetuspto-grants-2005_09
ORD IDord-c686b7b979604241baf46f71522022e3
Source noteuspto-grants-2005_09