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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2274117Generated: November 1, 2026

Ethanol → 4-Amino-6-{[1-(3-bromo-5-chloro-4-fluoro-2-methoxyphenyl)ethyl]amino}pyrimidine-5-carbonitrile

https://huagongshe.com/reaction/2274117

Reaction equation

Participants

RoleNameHCIDCharge
ReactantEthanolHCID 702—
ReactantDiisopropylethylamineHCID 81531—
Reactant4-Amino-6-chloropyrimidine-5-carbonitrileHCID 12278262—
Reactant1-(3-Bromo-5-chloro-4-fluoro-2-methoxyphenyl)ethanamineHCID 86666916—
Product4-Amino-6-{[1-(3-bromo-5-chloro-4-fluoro-2-methoxyphenyl)ethyl]amino}pyrimidine-5-carbonitrileHCID 8671146954%

Reaction Conditions

Temperature100 °C

Reaction Steps

A mixture of 1-(3-bromo-5-chloro-4-fluoro-2-methoxyphenyl)ethanamine (40 mg, 0.14 mmol), 4-amino-6-chloropyrimidine-5-carbonitrile (J & W PharmLab, #70-0156 33 mg, 0.21 mmol) and N,N-diisopropylethylamine (74 μL, 0.43 mmol) in ethanol (1.6 mL, 27 mmol) was heated at 100° C. overnight. Purification by preparative LC/MS (pH10) gave the desired compound (54% yield). LCMS calculated for C14H13BrClFN5O (M+H)+: m/z=400.0, 402.0. found: 400.0, 402.0. 1H NMR (300 MHz, DMSO-d6): δ 7.95 (s, 1H), 7.77 (m, 1H), 7.28 (br s, 2H), 5.56 (m, 1H), 3.92 (s, 1H), 1.40 (m, 3H).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09126948B2
Source datasetuspto-grants-2015_09
ORD IDord-22d9501d5b304e4baa3ea742a925fb54
Source noteuspto-grants-2015_09