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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2367339Generated: October 30, 2026

Sodium Carbonate → 4-(2-Amino-6-{2-[4-(4-chlorophenyl)-1H-imidazol-2-yl]-4-morpholinyl}-4-pyrimidinyl)-2-fluorobenzonitrile

https://huagongshe.com/reaction/2367339

Reaction equation

Participants

RoleNameHCIDCharge
ReactantSodium CarbonateHCID 10340—
Reactant2-Fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrileHCID 51350951—
ReactantHCID 178508446HCID 178508446—
CatalystHCID 178418397HCID 178418397—
SolventWaterHCID 962—
Solvent1,4-DioxaneHCID 31275—
Product4-(2-Amino-6-{2-[4-(4-chlorophenyl)-1H-imidazol-2-yl]-4-morpholinyl}-4-pyrimidinyl)-2-fluorobenzonitrileHCID 17850958083.6%

Reaction Conditions

Temperature140 °C

Reaction Steps

A mixture of 4-chloro-6-{2-[4-(4-chlorophenyl)-1H-imidazol-2-yl]-4-morpholinyl}-2-pyrimidinamine (300 mg, 0.767 mmol), 2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile (246 mg, 0.997 mmol), Na2CO3 (203 mg, 1.917 mmol) and Pd(PPh3)4 (89 mg, 0.077 mmol) in 1,4-dioxane (6 mL) and water (2 mL) was heated at 140° C. under microwave condition with stirring for 1 hour. The mixture was filtered, washed with EtOAc (150 mL), evaporated, and then chromatographed to afford the title compound (305 mg). LC-MS (ES) m/z=476 [M+H]+.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08697685B2
Source datasetuspto-grants-2014_04
ORD IDord-d65fb1d0c0684641bbea406a1b6efc5c
Source noteuspto-grants-2014_04