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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 632900Generated: October 30, 2026

Methanol → HCID 58072938, compound

https://huagongshe.com/reaction/632900

Reaction equation

Participants

RoleNameHCIDCharge
ReactantMethanolHCID 887—
ReactantCesium carbonateHCID 10796—
ReactantHCID 58073044HCID 58073044—
CatalystHCID 178418476HCID 178418476—
Solvent1,2-DimethoxyethaneHCID 8071—
ProductHCID 58072938HCID 58072938—

Reaction Conditions

Temperature80 °C

Reaction Steps

The title compound is synthesized in analogy to general procedure GP4 starting from 1.2 g (4.63 mmol) 4-chloro-6-ethyl-5-(6-amino-pyridin-3-ylethynyl)-pyrimidine using 1.0 g (5.6 mmol) 4-methoxycarbonyl-3-pyridyl boronic acid, 163 mg (0.23 mmol) bis-(triphenylphoshine)palladium(II) chloride, 7.0 mL (13.9 mmol) of an aqueous 2 M Cs2CO3 and 2 mL MeOH in 10 mL DME. The reaction mixture is stirred over night at 80° C. The reaction mixture is poured on water and washed with DCM. Aqueous 1 M HCl is added to the aqueous phase until pH 5 is reached. The precipitated product is filtered off and washed with water and methanol. After drying 290 mg (13%) of the desired product are obtained a solid material which is used for the next step without further purification.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09321771B2
Source datasetuspto-grants-2016_04
ORD IDord-70192b52d5944993a03ec34f675e0fd0
Source noteuspto-grants-2016_04