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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1801714Generated: October 31, 2026

Aniline → N4-(2-methyl-1H-indol-5-yl)-N2-phenylpyrimidine-2,4-diamine

https://huagongshe.com/reaction/1801714

Reaction equation

Participants

RoleNameHCIDCharge
ReactantAnilineHCID 6115—
ReactantN-(2-chloropyrimidin-4-yl)-2-methyl-1H-indol-5-amineHCID 59823198—
SolventWaterHCID 962—
SolventDimethylformamideHCID 6228—
ProductN4-(2-methyl-1H-indol-5-yl)-N2-phenylpyrimidine-2,4-diamineHCID 5982323285%

Reaction Conditions

Temperature60 °C

Reaction Steps

N-(2-chloropyrimidin-4-yl)-2-methyl-1H-indol-5-amine (0.1 mmol) and aniline (0.1 mmol) were dissolved in 0.5 ml DMF. To this was added p-TsOH monohydrate (0.2 mmol). The reaction mixture was stirred at 60° C. for 5 hours, diluted with water, and extracted with ethyl acetate. The organic layer was washed with water and brine sequentially, dried over anhydrous Na2SO4, and concentrated. The resulting residue was purified by column chromatography to provide the title product in a yield of 85%.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08349859B2
Source datasetuspto-grants-2013_01
ORD IDord-201534db299145be96d849d39e3fd9de
Source noteuspto-grants-2013_01