4-Pyrimidinamine, 2,5-dichloro-N-[2-[(1-methylethyl)sulfonyl]phenyl]- synthesis

6synthesis methods

Product Name:4-Pyrimidinamine, 2,5-dichloro-N-[2-[(1-methylethyl)sulfonyl]phenyl]-
CAS Number:761440-16-8
Molecular formula:C13H13Cl2N3O2S
Molecular Weight:346.23

76697-50-2

5750-76-5

4-Pyrimidinamine, 2,5-dichloro-N-[2-[(1-methylethyl)sulfonyl]phenyl]-

761440-16-8

To a flask containing 40 g (0.200 mol) 2-(isopropylsulfonyl)aniline (Formula-XI) in 400 mL of toluene solution under nitrogen protection were added 49.7 g (0.27 mol) 2,4,5-trichloropyrimidine (Formula-XII), 81.7 g (0.25 mol) cesium carbonate, 4.5 g (0.02 mol) palladium(II) acetate, and 13.1 g (0.05 mol) triphenylphosphine. The reaction mixture was heated to reflux under nitrogen atmosphere and maintained for 4 hours. The reaction was monitored by thin layer chromatography (TLC) to confirm that 2-(isopropylsulfonyl)aniline was completely consumed. Upon completion of the reaction, the mixture was cooled to 25-30 °C and filtered. The solids were washed with 400 mL of ethyl acetate. The filtrate and washings were combined and the crude product was obtained by removing toluene and ethyl acetate by distillation under reduced pressure at 60 °C. The crude product was purified by column chromatography to afford 45.6 g of 2,5-dichloro-N-(2-(isopropylsulfonyl)phenyl)pyrimidin-4-amine (formula-XIII) as a light yellow solid in 65.6% (theoretical) yield.

1493-27-2
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$5.00/10g

761440-16-8
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$9.00/250mg

Yield:-

Steps:

Multi-step reaction with 4 steps
1.1: potassium carbonate / N,N-dimethyl-formamide / 16 h / 100 °C
2.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 16 h / 20 °C
3.1: hydrogen / palladium 10% on activated carbon / methanol / 6 h
4.1: sodium hydride / N,N-dimethyl-formamide / 0.25 h / Cooling
4.2: 16 h / 20 °C

References:

WO2011/140338,2011,A1