N-bromobutanimide → 2-bromo-4-pentyl-1,4-dihydro-9H-[1,2,4]triazolo[1,5-a]purin-9-one

HRID 1664577Notes

Reaction equation

HRID 1664577 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]=[CH:17][N:18]=[C:7]12)[CH2:2][CH2:3][CH2:4][CH3:5].[Br:19]N1C(=O)CCC1=O>O1CCCC1>[Br:19][C:12]1[NH:11][C:10]2[C:9](=[O:15])[N:8]3[N:16]=[CH: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 576002184-pentyl-1,4-dihydro-9H-[1,2,4]triazolo[1,5-a]purin-9-one

Product 1

HCID 576002152-bromo-4-pentyl-1,4-dihydro-9H-[1,2,4]triazolo[1,5-a]purin-9-oneYield 12.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

To the mixture of 4-pentyl-1,4-dihydro-9H-[1,2,4]triazolo[1,5-a]purin-9-one (19 mg, 0.077 mmol) in tetrahydrofuran (10 mL) was added N-bromosuccinimide (20 mg, 0.12 mol) at rt. The mixture was stirred at 70° C. for 1 hour. The mixture was concentrated and purified by preparative LCMS to yield the desired product (3.10 mg, 12.4%). LCMS calculated for C11H14BrN6O (M+H): 325.0. found: 325.0, 327.0.

Workup

  1. concentrationThe mixture was concentrated
  2. custompurified by preparative LCMS

Sources & evidence

ORD record
ord-e9110266b18b4d67b8dc26486c737b02
Source dataset
uspto-grants-2011_10
Patent number
US08039478B2

Reaction notes

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