Potassium Carbonate → HCID 178519841, compound

2,4-dihydroxy-pyrimidin-5-carboxylic acid (125 mg, 0.80 mmol) was dissolved in N,N-dimethyl acetamide (3 ml) and then cooled to −150. Thionyl chloride (0.066 ml, 0.90 mmol) was added thereto at −15□ and the reaction mixture was stirred at −5□ for 20 minutes. The reaction mixture was cooled to −15□, and potassium carbonate (138 mg, 1.0 mmol) and 3,4-dihydro-2H-pyrido[4,3-b][1,4]oxazine (109 mg, 0.80 mmol) were added thereto dropwise. The reaction mixture was stirred at −5□ for 30 minutes, and then stirred at room temperature for 3 hours. After the completion of the reaction, water was added thereto and the mixture was extracted with ethyl acetate, and the combined organic layer was dried over anhydrous sodium sulfate (Na2SO4), filtered and evaporated under reduced pressure. The residue was purified by column chromatography on silica eluting with a solvent of dichloromethane:methanol=9:1. The fractions containing the product were collected and evaporated to obtain the target compound 59 as white solid (47 mg, 21%).

1. temperaturecooled to −150
2. additionwere added
3. stirringThe reaction mixture was stirred at −5□ for 30 minutes
4. stirringstirred at room temperature for 3 hours
5. additionwas added
6. extractionthe mixture was extracted with ethyl acetate
7. dry with materialthe combined organic layer was dried over anhydrous sodium sulfate (Na2SO4)
8. filtrationfiltered
9. customevaporated under reduced pressure
10. customThe residue was purified by column chromatography on silica eluting with a solvent of dichloromethane
11. additionThe fractions containing the product
12. customwere collected
13. customevaporated

ORD record

ord-00bd3060b9324f8eba84326f68b82326

Source dataset

uspto-grants-2013_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08394792B2