Phosphorus oxychloride → tert-butyl 4-(4-chloro-5H-pyrrolo[3,2-d]pyrimidin-7-yl)piperidine-1-carboxylate

温度

100 °C

tert-Butyl 4-(4-oxo-4,5-dihydro-3H-pyrrolo[3,2-d]pyrimidin-7-yl)piperidine-1-carboxylate (466 mg, 1.38 mmol) was dissolved in phosphorus oxychloride (2 mL) and stirred at 100° C. for 5 hours. The reaction liquid was concentrated under a reduced pressure, a 2 N aqueous sodium hydroxide solution (pH=14) was added, and then di-tert-butyl dicarbonate (602 mg, 2.76 mmol) was added to the aqueous solution, followed by stirring at room temperature for 2 hours. The reaction liquid was diluted with water, and extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate and concentrated under a reduced pressure. The obtained residue was purified by using silica gel chromatography (chloroform:methanol=10:1) to give tert-butyl 4-(4-chloro-5H-pyrrolo[3,2-d]pyrimidin-7-yl)piperidine-1-carboxylate (201 mg, 43.1%) as a pale yellow amorphous.

1. customThe reaction liquid
2. concentrationwas concentrated under a reduced pressure
3. additiona 2 N aqueous sodium hydroxide solution (pH=14) was added
4. stirringby stirring at room temperature for 2 hours
5. customThe reaction liquid
6. extractionextracted with ethyl acetate
7. washThe organic layer was washed with saturated brine
8. dry with materialdried over anhydrous sodium sulfate
9. concentrationconcentrated under a reduced pressure
10. customThe obtained residue was purified

ORDレコード

ord-094885f6d5cb42848982f09b51e413d7

出典データセット

uspto-grants-2014_07

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US08765771B2