Sodium hydride → 6-(1H-Indol-6-yloxy)pyrimidin-4-ylamine

Sodium hydride (200 mg, 5.00 mmol) was suspended in dimethyl sulfoxide (8 ml); while stirring at room temperature, 6-hydroxyindole (666 mg, 5.00 mmol) and 6-amino-4-chloropyrimidine (518 mg, 4.00 mmol) were added thereto one by one; and the reaction mixture was stirred at 60° C. for 2 hours, at 80° C. for 1 hour, and at 100° C. for 1.5 hours. After cooled down to room temperature, the reaction mixture was partitioned between ethyl acetate and water; and the organic layer was washed with brine, dried over anhydrous sodium sulfate, and concentrated. The residue was purified by silica gel column chromatography (Fuji Silysia BW-300, hexane:ethyl acetate=1:1, ethyl acetate, then ethyl acetate:methanol=98:2); the obtained crystals were suspended in ethyl acetate (50 ml) and stirred at room temperature overnight, filtered off, washed with diethyl ether, and dried to yield the title compound (322 mg, 1.42 mmol, 35.6%) as pale yellow crystals.

1. stirringand the reaction mixture was stirred at 60° C. for 2 hours, at 80° C. for 1 hour
2. temperatureAfter cooled down to room temperature
3. customthe reaction mixture was partitioned between ethyl acetate and water
4. washand the organic layer was washed with brine
5. dry with materialdried over anhydrous sodium sulfate
6. concentrationconcentrated
7. customThe residue was purified by silica gel column chromatography (Fuji Silysia BW-300, hexane
8. stirringstirred at room temperature overnight
9. filtrationfiltered off
10. washwashed with diethyl ether
11. customdried

ORD record

ord-9971943e308142718b302f119e856bec

Source dataset

uspto-grants-2008_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07468380B2