Water → Methyl 4-cyano-2-(4-ethylpiperazin-1-yl)-6-(m-tolylamino)pyrimidine-5-carboxylate

温度

90 °C

A mixture of methyl 4-chloro-2-(4-ethylpiperazin-1-yl)-6-(m-tolylamino)pyrimidine-5-carboxylate (152.6 mg, 0.391 mmol), tetrakis(triphenylphosphine)palladium (40.8 mg, 0.035 mmol) and zinc(II) cyanide (25.2 mg, 0.215 mmol) in DMF (3 mL) was stirred at 90° C. for 3 h. Water was added and the resulting mixture was extracted with EtOAc. The organic layers were washed with aq NaHCO3, water, and brine, were dried over anhydrous Na2SO4, and then filtered through SiO2. The filtrate was concentrated under reduced pressure and the residue was purified by column chromatography (SiO2 hexanes/EtOAc=5/1) to give the title compound as a yellow oil (51.1 mg, 34%). 1H NMR (500 MHz, CDCl3) δ ppm 1.12 (t, J=7.5 Hz, 3H), 2.35 (s, 3H), 2.44-2.49 (m, 6H), 3.81-3.98 (m, 7H), 6.95-6.96 (m, 1H), 7.23-7.26 (m, 1H), 7.37-7.47 (m, 2H), 10.46 (s, 1H). [M+H] calc'd for C20H25N6O2, 381; found, 381.

1. extractionthe resulting mixture was extracted with EtOAc
2. washThe organic layers were washed with aq NaHCO3, water, and brine
3. dry with materialwere dried over anhydrous Na2SO4
4. filtrationfiltered through SiO2
5. concentrationThe filtrate was concentrated under reduced pressure
6. customthe residue was purified by column chromatography (SiO2 hexanes/EtOAc=5/1)

ORDレコード

ord-d36e9ba6759c47aba41ad7950651b976

出典データセット

uspto-grants-2015_08

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US09108970B2