反应详情

A solution of N-(6-acetyl-2,4-dioxo-7-trifluoromethyl-1,4-dihydro-2H-quinazolin-3-yl)-methanesulfonamide (12.1 g, 33.1 mmol) in THF (150 mL)/MeOH (150 mL) under nitrogen was treated with sodium borohydride (25.0 g, 660 mmol) portionwise over 18 h at r.t. The suspension was then poured into a mixture of ice/concentrated EtOAc. The combined organic layers were dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The crude product was purified by column chromatography (silica gel 60, DCM/MeOH 9:1) affording colorless crystals, which were recrystallized in EtOAc to provide N-[6-(1-hydroxy-ethyl)-2,4-dioxo-7-trifluoromethyl-1,4-dihydro-2H-quinazolin-3-yl]-methanesulfonamide (8.85 g, 24.1 mmol, 73%) as a white powder, m.p. 263-268° C., 1H-NMR (DMSO-d6, 400 MHz) 8.41 (s, 1H), 7.49 (s, 1H), 5.66 (m, 1H), 5.03 (br s, 1H), 3.18 (s, 3H), 1.36 (d, J=6.2 Hz, 3H).

1. additionThe suspension was then poured into a mixture of ice/concentrated EtOAc
2. dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
3. filtrationfiltered
4. concentrationconcentrated in vacuo
5. customThe crude product was purified by column chromatography (silica gel 60, DCM/MeOH 9:1)
6. customaffording colorless crystals, which
7. customwere recrystallized in EtOAc