N-bromobutanimide → HCID 67177346, compound

Temperature

-50 °C

To a solution of 1.00 g (4.13 mmol) of 2-pyrimidin-4-yl-7,8,9,10-tetrahydro-6H-pyrimido[1,2-α]azepin-4-one (step 4.1 of example 4) in 35 mL of dry tetrahydrofuran at −50° C., was added 8.25 mL (8.25 mmol) of lithium bis(trimethylsilyl)amide (1M in tetrahydrofuran). The resulting mixture was stirred at −50° C. for 10 min. 0.808 g (4.54 mmol) of N-bromo-succinimide dissolved in 5 mL of tetrahydrofuran was added at −50° C. the resulting mixture was stirred for 1 hours. The mixture was dissolved in a saturated solution of ammonium chloride and ethyl acetate. The organic phases were washed with a saturated aqueous solution of sodium chloride, dried over sodium sulfate and evaporated to dryness. The residue was purified by flash chromatography (cyclohexane/ethyl acetate in proportions of 90/10) to afford 0.410 g (31%) of a white solid.

1. additionwas added at −50° C. the resulting mixture
2. stirringwas stirred for 1 hours
3. washThe organic phases were washed with a saturated aqueous solution of sodium chloride
4. dry with materialdried over sodium sulfate
5. customevaporated to dryness
6. customThe residue was purified by flash chromatography (cyclohexane/ethyl acetate in proportions of 90/10)

ORD record

ord-6d92892a86c747cba58fa3b313059a64

Source dataset

uspto-grants-2015_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09073914B2