Triethylamine → Tert-butyl 4-((4-amino-6-chloropyrimidin-5-yl)ethynyl)piperidine-1-carboxylate

To a degassed solution of Example 1A (400 mg, 1.6 mmol) in N,N-dimethylformamide (6 mL) was added copper (I) iodide (120 mg, 0.63 mmol) and triethylamine (2 mL, 14.33 mmol). The mixture was degassed for 5 minutes and tert-butyl 4-ethynylpiperidine-1-carboxylate (1.67 g, 7.98 mmol) and bis(triphenylphosphine) palladium(II)chloride (220 mg, 0.31 mmol) were added. The mixture was stirred at room temperature for 3 hours and diluted with water and extracted with ethyl acetate. The ethyl acetate layers were washed with water and brine, dried over sodium sulfate, filtered, and concentrated. Purification by column chromatography (silica gel, 30% ethyl acetate in hexane) afforded the title compound. LCMS: 337.1 (M+1)+.

1. customThe mixture was degassed for 5 minutes
2. extractionextracted with ethyl acetate
3. washThe ethyl acetate layers were washed with water and brine
4. dry with materialdried over sodium sulfate
5. filtrationfiltered
6. concentrationconcentrated
7. customPurification by column chromatography (silica gel, 30% ethyl acetate in hexane)

ORDレコード

ord-9649bca08b374e04b8d3fdf4f2fb6e53

出典データセット

uspto-grants-2016_05

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US09346813B2