N-bromobutanimide → HCID 25061973, compound

HRID 1787758Notes

Reaction equation

HRID 1787758 reaction equation
[CH3:1][S:2]([C:4]1[N:8]2[C:9](=[O:21])[C:10]3[NH:11][CH:12]=[N:13][C:14]=3[N:15]([CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])[C:7]2=[N:6][N:5]=1)=[O:3].CS(C1N2C(=O)C3NC=NC=3N(CCCCC)C2=NN=1)(=O)=O.[Br:44]N1C(=O)CCC1=O>C1COCC1.O>[Br:44][C:12]1[NH:11][C:10]2[C:9](=[O:21])[N:8]3[C:4]([S:2]([CH3:1])=[O:3])=[N:5][N:6]=[C:7]3[N:15]([CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])[C:14]=2[N:13]=1

Participants

6

Reactant 3

HCID 67184N-bromobutanimideHCID 57600187HCID 57600187, compoundHCID 57600296HCID 57600296, compound

Product 1

HCID 25061973HCID 25061973, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

To a mixture of 3-(methylsulfinyl)-9-pentyl-6,9-dihydro-5h-[1,2,4]triazolo[4,3-a]purin-5-one and 3-(methylsulfonyl)-9-pentyl-6,9-dihydro-5h-[1,2,4]triazolo[4,3-a]purin-5-one (3:2, 125 mg, 0.40 mmol) in THF (3 mL) was added N-bromosuccinimide (82.3 mg, 0.462 mmol). The mixture 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: C12H15BrN6O2S (M+H) 387.0; found: 387.0, 389.0.

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-b38acf7db3f4494abf390b4ea925799d
Source dataset
uspto-grants-2009_03
Patent number
US07511050B2

Reaction notes

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