Anisole → N-{5-[(5-amino-2-methylphenyl)amino][1,3]thiazolo[5,4-d]pyrimidin-2-yl}acetamide

A solution of tert-butyl(3-{[2-(acetylamino)[1,3]thiazolo[5,4-d]pyrimidin-5-yl]amino}-4-methylphenyl)carbamate (1.27 g, 3.06 mmol) and anisole (2 mL) in trifluoroacetic acid (20 mL) was stirred at 0° C. for 1 hr. The reaction mixture was concentrated under reduced pressure, saturated aqueous sodium hydrogen carbonate solution (50 mL) was added to the obtained residue, and the mixture was extracted with ethyl acetate/tetrahydrofuran mixture (1:1, 50 mL, 2×10 mL). The combined organic layer was washed with saturated brine (5 mL), and dried over anhydrous sodium sulfate. The insoluble material was filtered off, and the filtrate was concentrated under reduced pressure. The obtained residue was washed with ethyl acetate to give the title compound (795 mg, 83%) as a pale-green solid.

1. concentrationThe reaction mixture was concentrated under reduced pressure, saturated aqueous sodium hydrogen carbonate solution (50 mL)
2. additionwas added to the obtained residue
3. extractionthe mixture was extracted with ethyl acetate/tetrahydrofuran mixture (1:1, 50 mL, 2×10 mL)
4. washThe combined organic layer was washed with saturated brine (5 mL)
5. dry with materialdried over anhydrous sodium sulfate
6. filtrationThe insoluble material was filtered off
7. concentrationthe filtrate was concentrated under reduced pressure
8. washThe obtained residue was washed with ethyl acetate

ORD record

ord-65426867a9f246a290f3b114ee0568d1

Source dataset

uspto-grants-2013_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08344135B2