N-bromobutanimide → 2-Bromo-4-pentyl-1,4-dihydro-5H-[1,2,4]triazolo[5,1-i]purin-5-one

HRID 600604Notes

Reaction equation

HRID 600604 reaction equation
[CH2:1]([N:6]1[C:14]2[N:13]=[CH:12][NH:11][C:10]=2[C:9]2=[N:15][CH:16]=[N:17][N:8]2[C:7]1=[O:18])[CH2:2][CH2:3][CH2:4][CH3:5].[Br:19]N1C(=O)CCC1=O>C1COCC1>[Br:19][C:12]1[NH:11][C:10]2[C:9]3=[N:15][CH:16]=[N:17][N:8]3[C:7](=[O:18])[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 1359846844-Pentyl-1,4-dihydro-5H-[1,2,4]triazolo[5,1-i]purin-5-one

Product 1

HCID 1359551602-Bromo-4-pentyl-1,4-dihydro-5H-[1,2,4]triazolo[5,1-i]purin-5-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 4-pentyl-1,4-dihydro-5H-[1,2,4]triazolo[5,1-i]purin-5-one (20 mg, 0.081 mmol) in THF (5 mL) was added N-bromosuccinimide (19 mg, 0.11 mol). The reaction mixture was stirred at room temperature for 1 hour and then quenched by phenol. After removing solvent, the residue was purified by preparative LCMS (method B) to yield the desired product. 1HNMR (400 MHz, CD3OD): δ 8.30 (s, 1H), 4.30 (t, J=7.4 Hz, 2H), 1.86 (m, 2H), 1.41 (m, 4H), 0.93 (t, J=7.0 Hz, 3H). LCMS calculated for C11H14BrN6O (M+H): 325.0. found: 325.0, 327.0.

Workup

  1. customquenched by phenol
  2. customAfter removing solvent
  3. customthe residue was purified by preparative LCMS (method B)

Sources & evidence

ORD record
ord-bb92c94fe3a64ce3a18fe4307b8787a2
Source dataset
uspto-grants-2011_03
Patent number
US07902205B2

Reaction notes

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