N-bromobutanimide → HCID 25061712, compound

HRID 2368556Notes

Reaction equation

HRID 2368556 reaction equation
[CH3:1][C:2]1[N:6]2[C:7](=[O:19])[C:8]3[NH:9][CH:10]=[N:11][C:12]=3[N:13]([CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[C:5]2=[N:4][N:3]=1.[Br:20]N1C(=O)CCC1=O>C1COCC1>[Br:20][C:10]1[NH:9][C:8]2[C:7](=[O:19])[N:6]3[C:2]([CH3:1])=[N:3][N:4]=[C:5]3[N:13]([CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[C:12]=2[N:11]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 57600225HCID 57600225, compound

Product 1

HCID 25061712HCID 25061712, compoundYield 31%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 3-methyl-9-pentyl-6,9-dihydro-5H-[1,2,4]triazolo[4,3-a]purin-5-one (1.0 g, 3.8 mmol) in THF (50 mL) was added N-bromosuccinimide (0.75 g, 4.2 mol). The mixture was heated at 70° C. for 1 h and concentrated in vacuum. The residue was taken up in water and EtOAc. The organic layer was separated and the aqueous layer was extracted with ethyl acetate three times. The combined organic layers were dried (MgSO4), filtered, and concentrated in vacuum. The residue was purified by preparative LCMS to provide the desired product as a white powder (0.4 g, 30% yield). 1HNMR (400 MHz, d6-DMSO): δ 4.18 (t, J=7.5 Hz, 2H), 2.71 (s, 3H), 1.79 (m, 2H), 1.29 (m, 4H), 0.84 (m, 3H). LCMS calculated for C12H16BrN6O (M+H): 339.1, 341.1. Found: 339.1, 341.1.

Workup

  1. concentrationconcentrated in vacuum
  2. customThe organic layer was separated
  3. extractionthe aqueous layer was extracted with ethyl acetate three times
  4. dry with materialThe combined organic layers were dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuum
  7. customThe residue was purified by preparative LCMS

Sources & evidence

ORD record
ord-c8ff4f8d01624c099c841d844109c2b2
Source dataset
uspto-grants-2014_04
Patent number
US08703783B2

Reaction notes

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