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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2189199Generated: October 29, 2026

Water → HCID 58394337, compound

https://huagongshe.com/reaction/2189199

Reaction equation

Participants

RoleNameHCIDCharge
ReactantWaterHCID 962—
ReactantSodium CarbonateHCID 10340—
ReactantPhenylboronic AcidHCID 66827—
ReactantHCID 58394392HCID 58394392—
CatalystPalladium ChlorideHCID 24290—
CatalystFerrocene-1,1'-bis-(diphenylphosphine)HCID 635956—
Solvent1,2-DimethoxyethaneHCID 8071—
ProductHCID 58394337HCID 5839433782%

Reaction Steps

A mixture of (S)-tert-butyl 3-(5-bromo-2-chloropyrimidin-4-ylamino)pyrrolidine-1-carboxylate (0.200 g, 0.539 mmol), phenylboronic acid (0.077 g, 0.636 mmol), PdCl2.dPPf (0.019 g, 0.026 mmol) and 1 M aqueous Na2CO3 (1.06 mL, 1.06 mmol) in DME (5.3 mL) was refluxed for 16 hours. After cooling, water (50 mL) was added and the aqueous phase was extracted with diethyl ether (3×50 mL). The combined organic extracts were dried (MgSO4) and concentrated. The crude product was purified by silica gel chromatography (40% ethyl acetate/hexanes) to give the title compound as an oil (0.163 g, 82%).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08324226B2
Source datasetuspto-grants-2012_12
ORD IDord-48674ecd660346ed972a42e2c62b7ae9
Source noteuspto-grants-2012_12