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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2281369Generated: October 26, 2026

Sodium Carbonate → 2-chloro-N-cyclopropyl-5-(pyridin-4-yl)-7-tosyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine

https://huagongshe.com/reaction/2281369

Reaction equation

Participants

RoleNameHCIDCharge
ReactantSodium CarbonateHCID 10340—
Reactant(Pyridin-4-yl)boronic acidHCID 2734379—
Reactant2-chloro-N-cyclopropyl-5-iodo-7-tosyl-7H-pyrrolo[2,3-d]pyrimidin-4-amineHCID 57990325—
CatalystHCID 178418476HCID 178418476—
SolventWaterHCID 962—
Solvent1,4-DioxaneHCID 31275—
Product2-chloro-N-cyclopropyl-5-(pyridin-4-yl)-7-tosyl-7H-pyrrolo[2,3-d]pyrimidin-4-amineHCID 5799030289.8%

Reaction Conditions

Temperature100 °C

Reaction Steps

To a mixture of 2-chloro-N-cyclopropyl-5-iodo-7-tosyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine (0.3 g, 0.61 mmol), Pd(PPh3)2Cl2 (0.086 g, 0.122 mmol) and pyridine-4-ylboronic acid (0.165 g, 1.342 mmol) in dioxane (3 mL) was added a solution of Na2CO3 (0.2 g, 1.83 mmol) in water (1.5 mL). After degassing, the mixture was heated at 100° C. for 1.5 h. The mixture was purified by flash column chromatography (Hexane/EtOAc=1:1) to give 2-chloro-N-cyclopropyl-5-(pyridin-4-yl)-7-tosyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine (0.241 g).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09139581B2
Source datasetuspto-grants-2015_09
ORD IDord-f5f29b804400440490f5e77ebf718570
Source noteuspto-grants-2015_09