Bromine → (+/-)-9-Bromo-2-pyrimidin-4-yl-5,6,8,9-tetrahydro-7-oxa-1,4-a-diaza-benzocyclohepten-4-one

Temperatur

-40 °C

To a solution of 5.00 g (20.47 mmol) of pyrimidin-4-yl-5,6,8,9-tetrahydro-7-oxa-1,4a-diaza-benzocyclohepten-4-one in dry tetrahydrofuran (200 mL) under argon at −40° C. was added 22.52 mL (22.52 mmol) of lithium bis(trimethylsilyl)amide (1M in tetrahydrofuran). The solution was stirred at −40° C. for 10 min and 1.10 mL (21.49 mmol) of bromine was added rapidly. The reaction was stirred at −40° C. during 20 minutes and the reaction mixture was quenched with the addition of a saturated solution of ammonium chloride and extracted with ethyl acetate. The organic phase was washed with saturated sodium chloride solution and dried over sodium sulfate and concentrated. The residue was purified by flash chromatography (cyclohexane/ethyl acetate: 80/20 to 70/30) to afford 2.18 g (33%) of product.

1. stirringThe reaction was stirred at −40° C. during 20 minutes
2. customthe reaction mixture was quenched with the addition of a saturated solution of ammonium chloride
3. extractionextracted with ethyl acetate
4. washThe organic phase was washed with saturated sodium chloride solution
5. dry with materialdried over sodium sulfate
6. concentrationconcentrated
7. customThe residue was purified by flash chromatography (cyclohexane/ethyl acetate: 80/20 to 70/30)

ORD-Eintrag

ord-5f049757adf3446a847167f91016f2a1

Quelldatensatz

uspto-grants-2013_08

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08501728B2