反应详情

2-[Bis(tert-butoxycarbonyl)amino]-5-bromopyrimidine (2.00 g, 5.3 mmol) was dissolved in benzene (130 mL). 2-methylthiophenylboronic acid (2.24 g, 13.3 mmol), aq. sodium carbonate (13 mL, 2.0 M, 26 mmol), tetrabutyl ammonium bromide (86 mg, 0.26 mmol), and bis(triphenylphosphine)palladium(II)chloride (190 mg, 0.27 mmol) were added, and the resulting mixture was first purged with vacuum and argon, then refluxed 17 hours. The cooled mixture was diluted with EtOAc and water. The layers were separated, and the organic was dried over Na2SO4, filtered, and evaporated. The crude product was chromatographed on silica gel (50% EtOAc/hexanes), evaporated, and chromatographed a second time on silica gel (30-50% EtOAc/hexanes) to yield the desired product (2.13 g, 96%). 1H NMR (CDCl3): δ8.81 (s, 2H) , 7.41 (m, 2H) , 7.25 (m, 2H) , 2.39 (s, 3H), 1.49 (s, 18H).

1. customthe resulting mixture was first purged with vacuum and argon
2. temperaturerefluxed 17 hours
3. additionThe cooled mixture was diluted with EtOAc and water
4. customThe layers were separated
5. dry with materialthe organic was dried over Na2SO4
6. filtrationfiltered
7. customevaporated
8. customThe crude product was chromatographed on silica gel (50% EtOAc/hexanes)
9. customevaporated
10. customchromatographed a second time on silica gel (30-50% EtOAc/hexanes)