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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1038028Generated: October 31, 2026

Water → HCID 66940125, compound

https://huagongshe.com/reaction/1038028

Reaction equation

Participants

RoleNameHCIDCharge
ReactantWaterHCID 962—
ReactantEthyl AcetateHCID 8857—
ReactantTributylvinyltinHCID 81998—
Reactant1,1-Dimethylethyl (1S,4S)-5-(5-bromo-2-pyrimidinyl)-2,5-diazabicyclo[2.2.1]heptane-2-carboxylateHCID 58190411—
SolventDimethylformamideHCID 6228—
ProductHCID 66940125HCID 6694012535.7%

Reaction Conditions

Temperature90 °C

Reaction Steps

(S,S)-5-(5-Bromo-pyrimidin-2-yl)-2,5-diaza-bicyclo[2.2.1]heptane-2-carboxylic acid tert-butyl ester (177 mg, 0.5 mmol), tributyl vinyl tin (634 mg, 2 mmol) and Cl2Pd(dppf)CH2Cl2 (60 mg) was mixed in DMF (3 mL). The mixture was heated at 90° C. over 3 days. The cooled down reaction was participate between ethyl acetate (50 mL) and H2O (10 mL). The organic layer was washed with H2O (10 mL), brine (10 mL), dried (MgSO4) and filtered. The conc. filtrate was purified on silica gel column eluting with 33% to 50% ethyl acetate/hexanes to yield the title compound as a white solid (54 mg). MS (303, MH).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08546404B2
Source datasetuspto-grants-2013_10
ORD IDord-0b363c07576d4cf9b6ea41511d91155f
Source noteuspto-grants-2013_10