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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1892182Generated: October 31, 2026

Water → HCID 59404996, compound

https://huagongshe.com/reaction/1892182

Reaction equation

Participants

RoleNameHCIDCharge
ReactantWaterHCID 962—
ReactantN,N-DimethylpropargylamineHCID 81643—
ReactantHCID 59405025HCID 59405025—
CatalystCopper iodideHCID 83717—
CatalystHCID 178418476HCID 178418476—
SolventDimethylformamideHCID 6228—
SolventTriethylamineHCID 8471—
ProductHCID 59404996HCID 59404996109.8%

Reaction Conditions

Temperature75 °C

Reaction Steps

A solution of 2-amino-9-chloro-10-iodo-5,7-dihydro-6H-pyrimido[5,4-d][1]benzazepin-6-one (1.66 g, 4.29 mmol) and propargyl(dimethylamine) (0.74 mL, 6.89 mmol) in triethylamine (7 mL) and DMF (7 mL) was degassed with argon. To this solution was added bis(triphenylphosphine)palladium(II) chloride (0.30 g, 0.43 mmol) and copper iodide (0.163 g, 0.86 mmol). The reaction mixture was allowed to stir at 75° C. overnight. After the reaction mixture was allowed to cool to rt, water was added. The precipitate that formed was filtered and dried to give 2-amino-9-chloro-10-[3-(dimethylamino)prop-1-yn-1-yl]-5,7-dihydro-6H-pyrimido[5,4-d][1]benzazepin-6-one (1.61 g, 98%) as a brown solid. LCMS (FA): m/z=342 (M+H).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08507667B2
Source datasetuspto-grants-2013_08
ORD IDord-ac25258a35004de8b566a21c886b6ffd
Source noteuspto-grants-2013_08