2,6-Diaminopyridine → N2-(6-chloropyrimidin-4-yl)pyridine-2,6-diamine

Temperatur

100 °C

A mixture of 2,6-diaminopyridine (1.530 g, 14.020 mmol) and 4,6-dichloropyrimidine (2.610 g, 17.519 mmol) in 15 mL of n-butanol in a sealed vial was heated at 100° C. for 72 h. The dark brown sample was cooled, was concentrated to remove most of the n-butanol, and was then partitioned between EtOAc and sat. NaHCO3 solution. An emulsion formed, the sample was filtered through a pad of Celite and the layers were separated. The organic extract was washed with sat. KH2PO4 and brine solutions, was dried (MgSO4), was filtered and was concentrated to brown oily-solid. The sample was suspended into 50 mL of CH2Cl2, was cooled and was filtered to give 1.017 g of N-(6-chloro-pyrimidin-4-yl)-pyridine-2,6-diamine as yellow-orange solid. MS (ES) (m/z) 222/224 (M+1, 100/63%). TLC (SiO2, 50% EtOAc in hexanes): Rf 0.33.

1. temperatureThe dark brown sample was cooled
2. concentrationwas concentrated
3. customto remove most of the n-butanol
4. customwas then partitioned between EtOAc and sat. NaHCO3 solution
5. customAn emulsion formed
6. filtrationthe sample was filtered through a pad of Celite
7. customthe layers were separated
8. extractionThe organic extract
9. washwas washed with sat. KH2PO4 and brine solutions
10. dry with materialwas dried (MgSO4)
11. filtrationwas filtered
12. concentrationwas concentrated to brown oily-solid
13. temperaturewas cooled
14. filtrationwas filtered

ORD-Eintrag

ord-d7e4a78f983d4bbd92b5facf535089b1

Quelldatensatz

uspto-grants-2014_06

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08748606B2