Potassium Acetate → HCID 59627379, Verbindung

Temperatur

100 °C

A mixture of 9-(4-Methoxybenzyl)-6-bromo-9H-purine (2.7 g, 8.5 mmol), 2-fluoropyridin-3-ylboronic acid (1.8 g, 13 mmol) and potassium acetate (2.5 g, 25 mmol) in 1-butanol (50 mL) and water (10 mL) was purged with Ar (vacuum/purge three times) to remove oxygen, then PdCl2(PtBu2Ph)2 (0.063 g, 0.10 mmol) was added. The reaction mixture was stirred in a 100° C. oil bath for 45 min. The reaction mixture was allowed to cool to RT and diluted with Et2O (300 mL). The mixture was washed with water (2×100 mL), brine (50 mL), dried over Na2SO4, and filtered. Some product precipitated before the filtration so the Na2SO4 was washed with 3:1 CHCl3:IPA to dissolve all product. The combined filtrate was concentrated in vacuo to ˜50 mL as a suspension. The suspension was diluted with Et2O (200 mL) and hexane (200 mL) and the solid collected by suction filtration. The solid was washed with hexane (50 mL) and dried under a stream of N2 with vacuum suction for 14 h to afford 2.39 g (crop 1) as a pale orange fine crystalline solid. The mother liquors were concentrated in vacuo to ˜100 mL to afford a second crop of product. The second crop was collected by suction filtration, washed with hexane (100 mL) and dried under a stream of N2 as above to provide 200 mg (crop 2) as a pale orange fine crystalline solid. MS (ESI, pos. ion) m/z: 336.1 [M+H]+.

1. customwas purged with Ar (vacuum/purge three times)
2. customto remove oxygen
3. temperatureto cool to RT
4. washThe mixture was washed with water (2×100 mL), brine (50 mL)
5. dry with materialdried over Na2SO4
6. filtrationfiltered
7. customSome product precipitated before the filtration so the Na2SO4
8. washwas washed with 3:1 CHCl3
9. dissolutionIPA to dissolve all product
10. concentrationThe combined filtrate was concentrated in vacuo to ˜50 mL as a suspension
11. additionThe suspension was diluted with Et2O (200 mL) and hexane (200 mL)
12. filtrationthe solid collected by suction filtration
13. washThe solid was washed with hexane (50 mL)
14. dry with materialdried under a stream of N2 with vacuum suction for 14 h
15. customto afford 2.39 g (crop 1) as a pale orange fine crystalline solid
16. concentrationThe mother liquors were concentrated in vacuo to ˜100 mL
17. customto afford a second crop of product
18. filtrationThe second crop was collected by suction filtration
19. washwashed with hexane (100 mL)
20. dry with materialdried under a stream of N2 as above
21. customto provide 200 mg (crop 2) as a pale orange fine crystalline solid

ORD-Eintrag

ord-3af634a723234ca4a7d452213816f95e

Quelldatensatz

uspto-grants-2013_10

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08557830B2