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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 527988Generated: November 1, 2026

18-Crown-6 → tert-butyl 4-(4-chloro-7H-pyrrolo[2,3-d]pyrimidin-6-yl)piperidine-1-carboxylate

https://huagongshe.com/reaction/527988

Reaction equation

Participants

RoleNameHCIDCharge
Reactant18-Crown-6HCID 28557—
ReactantPotassium tert-butoxideHCID 23665647—
ReactantTert-butyl 4-((4-amino-6-chloropyrimidin-5-yl)ethynyl)piperidine-1-carboxylateHCID 90418839—
SolventTolueneHCID 1140—
SolventEthyl AcetateHCID 8857—
Producttert-butyl 4-(4-chloro-7H-pyrrolo[2,3-d]pyrimidin-6-yl)piperidine-1-carboxylateHCID 90418107—

Reaction Conditions

Temperature65 °C

Reaction Steps

To a solution of Example 1B (250 mg, 0.74 mmol), in toluene (5 mL), was added potassium tert-butoxide (249 mg, 2.22 mmol) followed by 18-crown-6 (15 mg, 0.057 mmol) and the mixture was heated under nitrogen at 65° C. for 12 hours. The mixture was cooled to room temperature, diluted with ethyl acetate, washed with water and brine, dried over sodium sulfate, filtered, concentrated and purified by column chromatography (silica gel, 40% ethyl acetate in hexane) to afford the title compound. LCMS: 337.1 (M+1)+.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09346813B2
Source datasetuspto-grants-2016_05
ORD IDord-7e65c9b42da0409e8ac89b9dd68e4146
Source noteuspto-grants-2016_05