反应详情

To a solution of 2-(phenylamino)pyrimidin-4(3H)-one (0.250 g, 1.34 mmol) in DMF (10 mL) was added LiH (0.012 g, 1.47 mmol). The reaction mixture was stirred for 25 minutes and then iodomethane (0.166 mL, 2.67 mmol) was added. The reaction was stirred at room temperature for 18 hours, the quenched with H2O and partitioned between EtOAc and saturated aqueous NaCl. The phases were separated, and the aqueous phase was re-extracted with EtOAc (1×). The combined organic layers were dried (Na2SO4), filtered and concentrated to yield a crude yellow oil. The crude product was purified by flash column chromatography, eluting with 30:1 dichloromethane/methanol. The desired product (0.166 g, 62%) was obtained as a white crystalline solid. 1H NMR (400 MHz, CDCl3) δ 7.68 (d, J=6.2 Hz, 1H), 7.46 (m, 2H), 7.39 (t, J=7.8 Hz, 2H), 7.19 (t, J=7.4 Hz, 1H), 6.48 (s, 1H), 6.01 (d, J=6.6 Hz, 1H), 3.58 (s, 3H). LRMS (ESI pos) m/e 202 (M+1).

1. stirringThe reaction was stirred at room temperature for 18 hours
2. customthe quenched with H2O
3. custompartitioned between EtOAc and saturated aqueous NaCl
4. customThe phases were separated
5. extractionthe aqueous phase was re-extracted with EtOAc (1×)
6. dry with materialThe combined organic layers were dried (Na2SO4)
7. filtrationfiltered
8. concentrationconcentrated
9. customto yield a crude yellow oil
10. customThe crude product was purified by flash column chromatography
11. washeluting with 30:1 dichloromethane/methanol