Hydrochloric Acid → 6-(5-Chloro-2-ethoxy-phenyl)-N*4*-p-tolyl-pyrimidine-2,4-diamine

To a stirred suspension of 4-chloro-6-(5-chloro-2-ethoxy-phenyl)-pyrimidin-2-ylamine (0.030 g, 0.106 mmol) in ethanol (5 ml) was added a solution of hydrogen chloride in dioxane (4.0 M, 0.015 ml) followed by p-tolylamine (0.014 g, 0.127 mmol). After heating under reflux for 3.5 hours, the volatiles were evaporated under reduced pressure. The residue was treated with 1.0 M hydrochloric acid (10 ml) and stirred overnight. After filtration, the solid was dissolved in methanol (10 ml) and treated with aqueous sodium carbonate solution (1.0 M, 1 ml). After stirring for 0.5 hours, the volatiles were evaporated under reduced pressure, the solid was stirred with water (10 ml) for 15 minutes, and filtered to provide the title compound (0.020 g, 53% yield) as a white powder. 1H NMR (DMSO-d6) δ 1.37 (t, 3H, J=6.8 Hz, CH3), 2.27 (s, 3H, CH3), 4.12 (q, 2H, J=6.6 Hz, CH2), 6.25 (s, 2H, NH2), 6.75 (s, 1H, Ar), 7.10-7.14 (m, 3H, Ar), 7.40-7.42 (m, 1H, Ar), 7.55 (d, 2H, J=8.0 Hz, Ar), 7.92 (s, 1H, Ar), 9.05 (s, 1H, NH).

1. temperatureAfter heating
2. temperatureunder reflux for 3.5 hours
3. customthe volatiles were evaporated under reduced pressure
4. additionThe residue was treated with 1.0 M hydrochloric acid (10 ml)
5. filtrationAfter filtration
6. dissolutionthe solid was dissolved in methanol (10 ml)
7. additiontreated with aqueous sodium carbonate solution (1.0 M, 1 ml)
8. stirringAfter stirring for 0.5 hours
9. customthe volatiles were evaporated under reduced pressure
10. stirringthe solid was stirred with water (10 ml) for 15 minutes
11. filtrationfiltered

ORD-Eintrag

ord-301de6b75a4347db8f7b5bd153a9d486

Quelldatensatz

uspto-grants-2008_09

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07419984B2