Aniline → 5-bromo-3-methyl-2-(phenylamino)pyrimidin-4(3H)-one

Temperatur

60 °C

A mixture of 5-bromo-2-chloro-3-methylpyrimidin-4(3H)-one (0.510 g, 2.282 mmol), aniline (0.271 ml, 2.967 mmol) and NaHCO3 (0.767 g, 9.129 mmol) in n-BuOH (15 mL) was stirred at 60° C. for 16 hours. The reaction mixture was cooled to room temperature and then diluted with EtOAc. The EtOAc layer was washed with H2O and saturated aqueous NaCl. The aqueous phase was re-extracted with EtOAc (1×). The combined EtOAc layers were dried (Na2SO4), filtered and concentrated to yield the desired product (0.636 g, 99%) as a pale yellow solid that was used without further purification. 1H NMR (400 MHz, DMSO-d6) δ 8.95 (br s, 1H), 7.94 (s, 1H), 7.47 (m, 2H), 7.35 (m, 2H), 7.14 (m, 1H), 3.53 (s, 3H). LRMS (ESI pos) m/e 280, 281 (M+, Br pattern).

1. temperatureThe reaction mixture was cooled to room temperature
2. washThe EtOAc layer was washed with H2O and saturated aqueous NaCl
3. extractionThe aqueous phase was re-extracted with EtOAc (1×)
4. dry with materialThe combined EtOAc layers were dried (Na2SO4)
5. filtrationfiltered
6. concentrationconcentrated

ORD-Eintrag

ord-164d2f6984ed4f8d8385e3c3dd543262

Quelldatensatz

uspto-grants-2011_08

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08003662B2