N-bromobutanimide → 6-bromo-4-pentyl-4,7-dihydro-8H-tetrazolo[1,5-a]purin-8-one

HRID 1664552Notes

Reaction equation

HRID 1664552 reaction equation
[CH2:1]([N:6]1[C:14]2[N:13]=[CH:12][NH:11][C:10]=2[C:9](=[O:15])[N:8]2[N:16]=[N:17][N:18]=[C:7]12)[CH2:2][CH2:3][CH2:4][CH3:5].C1C(=O)N([Br:26])C(=O)C1>C1COCC1>[Br:26][C:12]1[NH:11][C:10]2[C:9](=[O:15])[N:8]3[N:16]=[N:17][N:18]=[C:7]3[N:6]([CH2:1][CH2:2][CH2:3][CH2:4][CH3:5])[C:14]=2[N:13]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 576002974-pentyl-4,7-dihydro-8H-tetrazolo[1,5-a]purin-8-one

Product 1

HCID 250596546-bromo-4-pentyl-4,7-dihydro-8H-tetrazolo[1,5-a]purin-8-oneYield 13.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

The mixture of 4-pentyl-4,7-dihydro-8H-tetrazolo[1,5-a]purin-8-one (94.6 mg, 0.38 mmol) and NBS (75 mg, 0.42 mmol) in THF (20 ml) was stirred at 70° C. for 1 hour. After evaporation of solvent, the residue was purified by preparative LC-MS to yield the desired product (17.1 mg, 13.7%). LCMS calculated for C10H13BrN7O (M+H): 326.0. found: 326.0.

Workup

  1. customAfter evaporation of solvent
  2. customthe residue was purified by preparative LC-MS

Sources & evidence

ORD record
ord-8d0624b442ff46aca43c7c4f626d3f76
Source dataset
uspto-grants-2011_10
Patent number
US08039478B2

Reaction notes

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