Triethylamine → 6-bromo-2-(tetrahydrofuran-2-yl)thieno[3,2-d]pyrimidin-4(3H)-one

To a mixture of 3-amino-5-bromothiophene-2-carboxamide (120 mg) produced in Example 1, step D, triethylamine (0.083 mL) and tetrahydrofuran (3.0 mL) was added tetrahydrofuran-2-carbonylchloride (80 mg) with stirring at room temperature. The reaction mixture was stirred for 10 min, and the reaction system was concentrated under reduced pressure. 2M Aqueous sodium hydroxide solution (1.0 mL) was added to the residue, and the mixture was stirred with heating at 120° C. for 2 hr. The mixture was extracted with ethyl acetate, washed with brine and dried over anhydrous sodium sulfate. Insoluble material was removed by filtration, and the filtrate was concentrated under reduced pressure to give the title compound (160 mg) as a pale-yellow solid.

1. stirringThe reaction mixture was stirred for 10 min
2. concentrationthe reaction system was concentrated under reduced pressure
3. addition2M Aqueous sodium hydroxide solution (1.0 mL) was added to the residue
4. stirringthe mixture was stirred
5. temperaturewith heating at 120° C. for 2 hr
6. extractionThe mixture was extracted with ethyl acetate
7. washwashed with brine
8. dry with materialdried over anhydrous sodium sulfate
9. customInsoluble material was removed by filtration
10. concentrationthe filtrate was concentrated under reduced pressure

ORD record

ord-d5eb8d2962e241f4a2c9af1cd2398192

Source dataset

uspto-grants-2016_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09388195B2