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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 75916Generated: October 29, 2026

Diisopropylethylamine → 5-Chloro-2-{[1-(5-fluoropyrimidin-2-yl)ethyl]amino}-6-[(5-methyl-1H-pyrazol-3-yl)amino]nicotinonitrile

https://huagongshe.com/reaction/75916

Reaction equation

Participants

RoleNameHCIDCharge
ReactantDiisopropylethylamineHCID 81531—
Reactant(S)-N-((6-(5-Cyclopropyl-1H-pyrazol-3-ylamino)-5-fluoro-2-(1-(4-fluorophenyl)ethylamino)pyridin-3-yl)methyl)-2-morpholinoacetamideHCID 69285810—
ReactantHCID 86620614HCID 86620614—
Solvent1-ButanolHCID 263—
Product5-Chloro-2-{[1-(5-fluoropyrimidin-2-yl)ethyl]amino}-6-[(5-methyl-1H-pyrazol-3-yl)amino]nicotinonitrileHCID 6746039218.2%

Reaction Conditions

Temperature160 °C

Reaction Steps

A mixture of 1-(5-fluoropyrimidin-2-yl)ethanamine (Method 72, 0.05 g, 0.35 mmol), 2,5-dichloro-6-[(5-methyl-1H-pyrazol-3-yl)amino]nicotinonitrile (Method 60, 0.06 g, 0.25 mmol), and DIEA (0.12 ml, 0.7 mmol) in n-BuOH (10 ml) was charged into a microwave reaction vessel. The vessel was sealed and heated in microwave reactor at 160° C. for 6 hours. The solvent was removed under reduced pressure and the residue was purified by silica gel chromatography (DCM-EtOAc=1:1) to give the title compound as a yellow solid (0.017 g, 15%). LC-MS, 373 (M+1). 1H NMR (400 MHz, MeOD) δ 8.75 (s, 2H), 7.45 (s, 1H), 6.40 (s, 1H), 5.45 (br 1H), 2.35 (s, 3H), 1.60 (d, 3H).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08835465B2
Source datasetuspto-grants-2014_09
ORD IDord-a4c729850559471d9ce44ef84666204d
Source noteuspto-grants-2014_09