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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1633714Generated: October 31, 2026

Sodium Chloride → {4-[1-(4-Fluoro-phenyl)-1H-indol-5-yloxy]-butyl}-methyl-(2-methyl-pyrimidin-4-yl)-amine

https://huagongshe.com/reaction/1633714

Reaction equation

Participants

RoleNameHCIDCharge
ReactantSodium ChlorideHCID 5234—
ReactantDiisopropylethylamineHCID 81531—
Reactant4-Chloro-2-methylpyrimidineHCID 424447—
Reactant{4-[1-(4-Fluoro-phenyl)-1H-indol-5-yloxy]-butyl}-methylamineHCID 18679487—
SolventDimethylformamideHCID 6228—
Product{4-[1-(4-Fluoro-phenyl)-1H-indol-5-yloxy]-butyl}-methyl-(2-methyl-pyrimidin-4-yl)-amineHCID 1867956673.4%

Reaction Conditions

Temperature100 °C

Reaction Steps

20 mg (0.064 mmol) {4-[1-(4-Fluoro-phenyl)-1H-indol-5-yloxy]-butyl}-methylamine and 0.16 ml (0.96 mmol) N,N-diisopropyl ethyl amine in 1 ml of DMF were treated with 41 mg (0.32 mmol) 4-chloro-2-methylpyrimidine and stirred at 100° C. during 2 hours. After cooling to room temperature the mixture was treated with saturated aqueous NaCl and extracted three times with Et2O. Drying of the combined organic layers over Na2SO4, evaporation of the solvent and column chromatography on silica gel with EtOAc gave 19 mg (73%) {4-[1-(4-Fluoro-phenyl)-1H-indol-5-yloxy]-butyl}-methyl-(2-methyl-pyrimidin-4-yl)-amine as a light yellow oil, MS: 405 (MH+).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS06503907B2
Source datasetuspto-grants-2003_01
ORD IDord-e0519721f87541c1a968fdb9b4b9485a
Source noteuspto-grants-2003_01