N-bromobutanimide → 7-bromo-3-(methylthio)-9-pentyl-6,9-dihydro-5H-[1,2,4]triazolo[4,3-a]purin-5-one

HRID 2368560Notes

Reaction equation

HRID 2368560 reaction equation
[CH3:1][S:2][C:3]1[N:7]2[C:8](=[O:20])[C:9]3[NH:10][CH:11]=[N:12][C:13]=3[N:14]([CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[C:6]2=[N:5][N:4]=1.[Br:21]N1C(=O)CCC1=O>C1COCC1.O>[Br:21][C:11]1[NH:10][C:9]2[C:8](=[O:20])[N:7]3[C:3]([S:2][CH3:1])=[N:4][N:5]=[C:6]3[N:14]([CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[C:13]=2[N:12]=1

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 576003133-(methylthio)-9-pentyl-6,9-dihydro-5H-[1,2,4]triazolo[4,3-a]purin-5-one

Product 1

HCID 250619727-bromo-3-(methylthio)-9-pentyl-6,9-dihydro-5H-[1,2,4]triazolo[4,3-a]purin-5-one

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 3-(methylthio)-9-pentyl-6,9-dihydro-5h-[1,2,4]triazolo[4,3-a]purin-5-one (111 mg, 0.380 mmol), N-bromosuccinimide (81.1 mg, 0.456 mmol) in THF (3 ml) was stirred at 70° C. for 3 hours. The reaction was diluted with water and extracted with ethyl acetate three times, dried with sodium sulfate, filtered, and concentrated in vacuo. The crude residue was purified by Prep LCMS to yield the desired product. LCMS calculated for: C12H16BrN6OS (M+H) 371.0. Found: 371.0, 373.0.

Workup

  1. extractionextracted with ethyl acetate three times
  2. dry with materialdried with sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe crude residue was purified by Prep LCMS

Sources & evidence

ORD record
ord-681848133d6c45a3b115a02410bd8708
Source dataset
uspto-grants-2014_04
Patent number
US08703783B2

Reaction notes

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