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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1257786Generated: November 3, 2026

Potassium Carbonate → 4-(2-aminopyrimidin-5-yl)-2-fluoro-N-methylbenzamide

https://huagongshe.com/reaction/1257786

Reaction equation

Participants

RoleNameHCIDCharge
ReactantPotassium CarbonateHCID 11430—
Reactant2-Aminopyrimidine-5-boronic acid, pinacol esterHCID 17750212—
ReactantBenzamide, 4-bromo-2-fluoro-N-methyl-HCID 24694329—
CatalystHCID 178418397HCID 178418397—
SolventEthanolHCID 702—
SolventWaterHCID 962—
SolventTolueneHCID 1140—
Product4-(2-aminopyrimidin-5-yl)-2-fluoro-N-methylbenzamideHCID 6722454891.4%

Reaction Conditions

Temperature110 °C

Reaction Steps

A mixture of 4-bromo-2-fluoro-N-methylbenzamide (900 mg, 3.9 mmol), 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidin-2-amine (710 mg, 3.2 mmol), tetrakis(triphenylphosphine)palladium (100 mg, 0.1 mmol) and potassium carbonate (1.3 g, 9.7 mmol) in toluene (6.0 mL) and ethanol (3.0 mL) and water (3.0 mL) was heated at 110° C. for 2 hours. After cooling to RT, the reaction mixture was quenched with water and extracted with diethyl ether. The solid was filtered and washed with water and diethyl ether to afford the desired product (720 mg).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08461330B2
Source datasetuspto-grants-2013_06
ORD IDord-bb0e185e61f544f5a8410172b71fdb8a
Source noteuspto-grants-2013_06