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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2361006Generated: October 31, 2026

1,2-Dimethoxyethane → 2-Chloro-4-(2-chloropyridin-3-yl)pyrimidine

https://huagongshe.com/reaction/2361006

Reaction equation

Participants

RoleNameHCIDCharge
Reactant1,2-DimethoxyethaneHCID 8071—
Reactant2,4-DichloropyrimidineHCID 77531—
ReactantSodium BicarbonateHCID 516892—
Reactant(2-Chloropyridin-3-yl)boronic acidHCID 2762704—
CatalystHCID 178418397HCID 178418397—
SolventEthyl AcetateHCID 8857—
Product2-Chloro-4-(2-chloropyridin-3-yl)pyrimidineHCID 24901930—

Reaction Conditions

Temperature90 °C

Reaction Steps

To 2,4-dichloropyrimidine (2.00 g, 13.4 mmol), 2-choropyridine-3-boronic acid (3.16 g, 20.1 mmol) and Pd(PPh3)4 (1.55 g, 1.30 mmol), was added DME (30.0 mL) and 1 M NaHCO3 (13.0 mL). The resulting mixture was heated to 90° C. for 17 hours, then diluted with EtOAc and extracted with saturated sodium carbonate, water, and brine. The organics were dried over sodium sulfate, filtered and concentrated. The resulting solid was triturated with ether and dried to yield the desired product. MS m/z=226 [M+H]+. Calc'd for C9H5Cl2N4: 225.12.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08686155B2
Source datasetuspto-grants-2014_04
ORD IDord-ad159907f21d468db1c72097b8d6adc8
Source noteuspto-grants-2014_04