Triethylamine → (3-Chloro-4-methoxy-phenyl)-(4,6-dichloro-pyrimidin-2-yl)-amine

To a solution of 2,4,6-trichloro-pyrimidine (0.29 g, 1.58 mmol) in 1:1 chloroform-hexane (10 mL) was added 3-chloro-p-anisidine (0.5 g, 3.1 mmol) at 25° C. with stirring. To this was added triethylamine (0.22 mL, 1.59 mmol) at 25° C. and the mixture was heated and refluxed for 7 hours under nitrogen atmosphere. The mixture was then concentrated under vacuum, diluted with cold water (30 mL) and extracted with ethyl acetate (2×60 mL). The organic layers were collected, combined, washed with brine (30 mL), dried over anhydrous sodium sulphate, and concentrated under vacuum. The crude product thus obtained was purified by column chromatography using ethyl acetate-petroleum ether to afford the desired compound. Yield: 22%.

1. temperaturethe mixture was heated
2. temperaturerefluxed for 7 hours under nitrogen atmosphere
3. concentrationThe mixture was then concentrated under vacuum
4. additiondiluted with cold water (30 mL)
5. extractionextracted with ethyl acetate (2×60 mL)
6. customThe organic layers were collected
7. washwashed with brine (30 mL)
8. dry with materialdried over anhydrous sodium sulphate
9. concentrationconcentrated under vacuum
10. customThe crude product thus obtained
11. customwas purified by column chromatography

ORD record

ord-be9ab0e62d56432f96749a77f95e855d

Source dataset

uspto-grants-2010_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07820654B2