Pyridine → 6-bromo-4-(phenylcarbonyl)-1,2,4-triazine-3,5(2H,4H)-dione

HRID 1513333Notes

Reaction equation

C([N:4]1[C:9](=[O:10])[NH:8][C:7](=[O:11])[C:6]([Br:12])=[N:5]1)(=O)C.N1C=CC=CC=1.[C:19](Cl)(=[O:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>O1CCOCC1.CCOC(C)=O>[Br:12][C:6]1[C:7](=[O:11])[N:8]([C:19]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[O:26])[C:9](=[O:10])[NH:4][N:5]=1

Participants

Conditions

Temperature: 5 °C

Procedure

2-acetyl-6-bromo-1,2,4-triazine-3,5(2H,4H)-dione (P6, 2.47 g, 10.56 mmol) was dissolved in 1,4-Dioxane (18 ml) and pyridine (2.56 ml, 31.7 mmol). The solution was cooled to 5° C. then benzoyl chloride (1.470 ml, 12.67 mmol) was added dropwise and the mixture was stirred at room temperature overnight. The day after the reaction mixture was diluted with AcOEt and washed with 0.5N HCl aq solution. Organic phase was separated, dried over Na2SO4, filtered and concentrated under reduced pressure. Crude product (brown oil) was purified by flash chromatography (SiO2, eluent: Cy to Cy/AcOEt 6:4) affording 6-bromo-4-(phenylcarbonyl)-1,2,4-triazine-3,5(2H,4H)-dione (1.46 g, 4.93 mmol, 46.7% yield) as a white powder.

Workup

washwashed with 0.5N HCl aq solution
customOrganic phase was separated
dry with materialdried over Na2SO4
filtrationfiltered
concentrationconcentrated under reduced pressure
customCrude product (brown oil) was purified by flash chromatography (SiO2, eluent: Cy to Cy/AcOEt 6:4)

Sources & evidence

ORD record: ord-bdefdbeffe234d45a9baf203bfcb8f58
Source dataset: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08217168B2

Reaction notes

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