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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 339997Generated: October 29, 2026

Diisopropylethylamine → ethyl 2-(4-chloro-1-methyl-1H-pyrazol-5-yl)-4-methylpyrimidine-5-carboxylate

https://huagongshe.com/reaction/339997

Reaction equation

Participants

RoleNameHCIDCharge
ReactantDiisopropylethylamineHCID 81531—
ReactantEthyl 2-chloro-4-methylpyrimidine-5-carboxylateHCID 21220624—
Reactant4-chloro-1-methyl-5-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 75525667—
CatalystHCID 178418851HCID 178418851—
SolventWaterHCID 962—
Solvent1,4-DioxaneHCID 31275—
Productethyl 2-(4-chloro-1-methyl-1H-pyrazol-5-yl)-4-methylpyrimidine-5-carboxylateHCID 8668148359.4%

Reaction Conditions

Temperature110 °C

Reaction Steps

A mixture of 4-chloro-1-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (1.45 g, 5.98 mmol), ethyl 2-chloro-4-methylpyrimidine-5-carboxylate (0.999 g, 4.98 mmol), bis(tri-t-butylphosphine)palladium (509 mg, 0.996 mmol), and N,N-diisopropylethylamine (1.74 mL, 9.98 mmol) in 1,4-dioxane (10 mL) and water (0.5 mL) was stirred at 110° C. for 40 mins under microwave. Direct purification by combi-flash chromatography afforded 0.83 g (59% yield) of the desired product. LC-MS found: 281.1 (M+H)+.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08895571B2
Source datasetuspto-grants-2014_11
ORD IDord-640811577481449ea52aa1dd4167d370
Source noteuspto-grants-2014_11