Dichloromethane → HCID 59291169, compound

K2CO3 (10.60 g, 76.68 mmol) was added to a mixture of 4-[(E)-2-butoxyethenyl]-2-chloro-5-methylpyrimidine (Intermediate 6, 6.95 g, 30.67 mmol) and 1-aminopyridinium iodide (9.19 g, 41.40 mmol) in DMF (40 mL) at r.t. The resulting dark blue suspension was stirred at r.t. for 3 days (became deep red color) and was then heated at 110° C. for 3 h. The mixture was then cooled, diluted with EtOAc (100 mL) plus a little CH2Cl2. This solution was washed with water (100 mL) and the aqueous wash solution was extracted with EtOAc (100 mL). The combined organic solutions were washed with water (4×100 mL) and sat. brine (50 mL), dried (MgSO4) and concentrated in vacuo. The residue was dissolved in THF (100 mL) and filtered through a 30 g silica pad. The eluted solution was concentrated in vacuo and the residue was washed with −70° C. CH3OH to give the title compound (2.223 g, 30%) as a beige crystalline solid; 1H NMR: 2.53 (3H, s), 7.22 (1H, m), 7.64 (1H, m), 8.53-8.59 (2H, m), 8.70 (1H, s), 8.90 (1H, d); m/z: ES+ MH+ 245.

1. temperaturewas then heated at 110° C. for 3 h
2. temperatureThe mixture was then cooled
3. washThis solution was washed with water (100 mL)
4. extractionthe aqueous wash solution was extracted with EtOAc (100 mL)
5. washThe combined organic solutions were washed with water (4×100 mL) and sat. brine (50 mL)
6. dry with materialdried (MgSO4)
7. concentrationconcentrated in vacuo
8. dissolutionThe residue was dissolved in THF (100 mL)
9. filtrationfiltered through a 30 g silica pad
10. concentrationThe eluted solution was concentrated in vacuo
11. washthe residue was washed with −70° C

ORD record

ord-8aed614ef6804e8690c8aaa96d7fecfb

Source dataset

uspto-grants-2015_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08946235B2