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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2204397Generated: October 30, 2026

(2,4-Dimethoxypyrimidin-5-yl)boronic acid → 5-(5-Chloro-2-fluoro-1-methyl-6-oxo-1,6-dihydro-pyridin-3-yl)-6-(4-chloro-phenyl)-2-(2,4-dimethoxy-pyrimidin-5-yl)-1-isopropyl-5,6-dihydro-1H-pyrrolo[3,4-b]pyrrol-4-one

https://huagongshe.com/reaction/2204397

Reaction equation

Participants

RoleNameHCIDCharge
Reactant(2,4-Dimethoxypyrimidin-5-yl)boronic acidHCID 2736209—
Reactant4-Methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidin-2-amineHCID 59198404—
Reactant2-Bromo-5-(5-chloro-2-fluoro-1-methyl-6-oxo-1,6-dihydro-pyridin-3-yl)-6-(4-chloro-phenyl)-1-isopropyl-5,6-dihydro-1H-pyrrolo[3,4-b]pyrrol-4-oneHCID 86703143—
Reactant2-bromo-5-(5-chloro-2-methyl-phenyl)-6-(4-chloro-phenyl)-1-isopropyl-5,6-dihydro-1H-pyrrolo[3,4-b]pyrrol-4-oneHCID 86703169—
Product5-(5-Chloro-2-fluoro-1-methyl-6-oxo-1,6-dihydro-pyridin-3-yl)-6-(4-chloro-phenyl)-2-(2,4-dimethoxy-pyrimidin-5-yl)-1-isopropyl-5,6-dihydro-1H-pyrrolo[3,4-b]pyrrol-4-oneHCID 86703208—

Reaction Steps

The title compound was prepared in analogy to the procedure described for Example 25 but 2-bromo-5-(5-chloro-2-fluoro-1-methyl-6-oxo-1,6-dihydro-pyridin-3-yl)-6-(4-chloro-phenyl)-1-isopropyl-5,6-dihydro-1H-pyrrolo[3,4-b]pyrrol-4-one (Intermediate AT) and 2,4-dimethoxypyrimidine-5-boronic acid were used instead of 2-bromo-5-(5-chloro-2-methyl-phenyl)-6-(4-chloro-phenyl)-1-isopropyl-5,6-dihydro-1H-pyrrolo[3,4-b]pyrrol-4-one and 4-methoxy-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-pyrimidin-2-ylamine respectively. The title compound was obtained as a light pink foam. ESI-MS: tR=1.08 min, [M+H]+ 572/574/576 (LC-MS 1); TLC: Rf=0.14 (4:1 EtOAc/heptanes).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09365576B2
Source datasetuspto-grants-2016_06
ORD IDord-7b84972667c247139a0c49c03dc6fa77
Source noteuspto-grants-2016_06