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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1482688Generated: October 26, 2026

Diisopropylethylamine → N-(2-(benzyloxy)-5-nitrophenyl)-2-chloro-5-fluoropyrimidin-4-amine

https://huagongshe.com/reaction/1482688

Reaction equation

Participants

RoleNameHCIDCharge
ReactantDiisopropylethylamineHCID 81531—
Reactant2,4-Dichloro-5-fluoropyrimidineHCID 250705—
Reactant2-(Benzyloxy)-5-nitroanilineHCID 264603—
ReactantEthyl acetate hexane methylene-chlorideHCID 21942482—
Solvent1-ButanolHCID 263—
SolventWaterHCID 962—
ProductN-(2-(benzyloxy)-5-nitrophenyl)-2-chloro-5-fluoropyrimidin-4-amineHCID 8672434325.1%

Reaction Conditions

Temperature120 °C

Reaction Steps

In a pressure tube 2-(benzyloxy)-5-nitroaniline (0.65 g), 2,4-dichloro-5-fluoropyrimidine (0.66 g) and DIPEA (0.69 g) were taken in n-butanol (10 mL). The reaction mixture was heated at 120° C. for 24 hr. The reaction was monitored on TLC using DCM:hexane:ethyl acetate (3:5:2) as mobile phase. The reaction was complete after 24 h. After completion, reaction mixture was allowed to cool at room temperature. The reaction was poured into water and extracted with ethyl acetate (3×25 mL). The ethyl acetate layer washed with brine solution, dried over sodium sulfate and concentrated under reduced pressure at 40° C. Crude material was purified by triturating with diethyl ether to give 0.25 g of N-(2-(benzyloxy)-5-nitrophenyl)-2-chloro-5-fluoropyrimidin-4-amine. M+1=374.8.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09415049B2
Source datasetuspto-grants-2016_08
ORD IDord-6fdbeb31999a41918e8b0fc24bf2f550
Source noteuspto-grants-2016_08