Triethylamine → 6-bromo-2-(2-pyrrolidin-1-ylethyl)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 3-chloropropanoyl chloride (0.057 mL) with stirring at room temperature. After 10 min, pyrrolidine (0.23 mL) was added, and the mixture was stirred at room temperature for 10 min. 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 1 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 (131 mg) as a pale-yellow solid.

1. stirringthe mixture was stirred at room temperature for 10 min
2. concentrationThe reaction system was concentrated under reduced pressure, 2M aqueous sodium hydroxide solution (1.0 mL)
3. additionwas added to the residue
4. stirringthe mixture was stirred
5. temperaturewith heating at 120° C. for 1 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-d9d22358c6c14e14af1bff5bfc8e95bc

Source dataset

uspto-grants-2016_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09388195B2