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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1471973Generated: October 29, 2026

Sodium Hydroxide → 5-Chloro-N2-[4-(dimethylphosphoryl)-2-ethylphenyl]-N4-[2-(propan-2-ylsulfonyl)phenyl]pyrimidine-2,4-diamine

https://huagongshe.com/reaction/1471973

Reaction equation

Participants

RoleNameHCIDCharge
ReactantSodium HydroxideHCID 14798—
Reactant2,5-dichloro-N-(2-((1-methylethyl)sulfonyl)phenyl)-4-pyrimidinamineHCID 59764378—
Reactant4-(Dimethylphosphoryl)-2-ethylanilineHCID 67052679—
Solvent2-MethoxyethanolHCID 8019—
Product5-Chloro-N2-[4-(dimethylphosphoryl)-2-ethylphenyl]-N4-[2-(propan-2-ylsulfonyl)phenyl]pyrimidine-2,4-diamineHCID 6882814340.4%

Reaction Conditions

Temperature90 °C

Reaction Steps

To a solution of 2,5-dichloro-N-[2-(propan-2-ylsulfonyl)phenyl]pyrimidin-4-amine (as prepared in Example 17: 0.079 g, 0.22 mmol) in 1.5 mL of 2-methoxyethanol was added 4-(dimethylphosphoryl)-2-ethylaniline (0.050 g, 0.21 mmol) as its hydrochloride salt. The mixture was heated in a sealed tube at 90° C. for 16 h. The mixture was basified with 1N NaOH solution, and extracted with ethyl acetate. The organic layers were combined, washed with saturated sodium chloride solution, dried with sodium sulfate, filtered and concentrated. The crude residue was purified by prep-HPLC to afford the final compound (43 mg, 40% yield). MS/ES+: m/z=507.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09012462B2
Source datasetuspto-grants-2015_04
ORD IDord-eaa8d315953e479e803e1c0a7133356b
Source noteuspto-grants-2015_04