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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1627221Generated: November 1, 2026

Diisopropylethylamine → 3-(1-(2-chloro-9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-ylamino)ethyl)-8-methyl-2-phenylisoquinolin-1(2H)-one

https://huagongshe.com/reaction/1627221

Reaction equation

Participants

RoleNameHCIDCharge
ReactantDiisopropylethylamineHCID 81531—
Reactant2,6-Dichloro-9-(tetrahydro-2H-pyran-2-yl)-9H-purineHCID 270265—
Reactant(S)-3-(1-aminoethyl)-8-methyl-2-phenylisoquinolin-1(2H)-oneHCID 58008747—
Reactant3-(1-(2-chloro-9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-ylamino)ethyl)-8-methyl-2-phenylisoquinolin-1(2H)-oneHCID 86637170—
Solvent1-ButanolHCID 263—
Product3-(1-(2-chloro-9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-ylamino)ethyl)-8-methyl-2-phenylisoquinolin-1(2H)-oneHCID 8663717046%
ProductHCID 178423763HCID 178423763—

Reaction Conditions

Temperature120 °C

Reaction Steps

3-(1-Aminoethyl)-8-methyl-2-phenylisoquinolin-1(2H)-one (compound 4704) (200 mg, 0.72 mol), 2,6-dichloro-9-(tetrahydro-2H-pyran-2-yl)-9H-purine (compound 5302) (393 mg, 1.44 mmol) and DIPEA (279 mg, 2.16 mmol) were dissolved in n-BuOH (20 mL) in a sealed tube, and the resulting mixture was stirred at 120° C. for 16 h. The reaction mixture was concentrated in vacuo and the residue was purified by flash column chromatography on silica gel (eluting with 30% to 50% Hex/EA) to afford the desired product, 3-(1-(2-chloro-9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-ylamino)ethyl)-8-methyl-2-phenylisoquinolin-1(2H)-one (compound 5303) (172 mg, 46% yield) as a white solid.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08785456B2
Source datasetuspto-grants-2014_07
ORD IDord-b2a3c60ca92a4a83b66c516885b96761
Source noteuspto-grants-2014_07