Tetra-n-butylammonium tribromide → HCID 86727335, Verbindung

Temperatur

25 °C

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).

1. customthe resulting reaction mixture
2. customThe reaction was quenched by addition of saturated aqueous sodium thiosulphate (10 mL)
3. additionThe mixture was neutralized by the addition of saturated aqueous NaHCO3
4. additiondiluted with water (100 mL)
5. extractionextracted with DCM (3×50 mL)
6. concentrationThe combined organic layer was concentrated
7. washwashed with brine (3×30 mL)
8. dry with materialdried over anhydrous Na2SO4
9. filtrationfiltered
10. concentrationconcentrated
11. customto give the crude product, which
12. customwas purified by column chromatography on silica gel (eluting with 5% MeOH in DCM)

ORD-Eintrag

ord-a7306a7dd0b84378a9e77184d40a1479

Quelldatensatz

uspto-grants-2015_08

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US09115151B2