반응 #606389

반응 방정식

6-amino-4-methyl-2,10-dihydro-9-oxa-1,2,4a-triaza-phenanthren-3-one

tetrabutylammonium tribromide

→

6-amino-7-bromo-4-methyl-2,10-dihydro-9-oxa-1,2,4a-triaza-phenanthren-3-one

수율 46.0%

용매

MeOH

DCM

반응 조건

후처리

1. 1
   기타the resulting reaction mixture
2. 2
   기타The reaction was quenched by addition of saturated aqueous sodium thiosulphate (10 mL)
3. 3
   workup.ADDITIONThe mixture was neutralized by the addition of saturated aqueous NaHCO3
4. 4
   workup.ADDITIONdiluted with water (100 mL)
5. 5
   추출extracted with DCM (3×50 mL)
6. 6
   농축The combined organic layer was concentrated
7. 7
   세척washed with brine (3×30 mL)
8. 8
   건조dried over anhydrous Na2SO4
9. 9
   여과filtered
10. 10
    농축concentrated
11. 11
    기타to give the crude product, which
12. 12
    기타was purified by column chromatography on silica gel (eluting with 5% MeOH in DCM)

실험 절차

To a solution of 6-amino-4-methyl-2,10-dihydro-9-oxa-1,2,4a-triaza-phenanthren-3-one (5.0 g, 21.5 mmol) in MeOH (20 mL) and DCM (40 mL) was added tetrabutylammonium tribromide (10.9 g, 22.6 mmol) portionwise and the resulting reaction mixture was stirred for 0.5 h at 25° C. The reaction was quenched by addition of saturated aqueous sodium thiosulphate (10 mL). The mixture was neutralized by the addition of saturated aqueous NaHCO3, diluted with water (100 mL) and extracted with DCM (3×50 mL). The combined organic layer was concentrated, washed with brine (3×30 mL), dried over anhydrous Na2SO4, filtered and concentrated to give the crude product, which was purified by column chromatography on silica gel (eluting with 5% MeOH in DCM) to give 6-amino-7-bromo-4-methyl-2,10-dihydro-9-oxa-1,2,4a-triaza-phenanthren-3-one (3.0 g, 46%) as a brown solid. 1H NMR (DMSO-d6, 400 MHz): δ 10.78 (s, 1H), 7.02 (s, 1H), 6.68 (s, 1H), 4.98 (brs, 2H), 4.50 (m, 3H), 1.31 (d, J=6.8 Hz, 3H).

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