Phenol → 2-bromo-4-pentyl-8-phenyl-1,4-dihydro-5H-[1,2,4]triazolo[5,1-i]purin-5-one

HRID 600586Notes

Reaction equation

HRID 600586 reaction equation
[CH2:1]([N:6]1[C:14]2[N:13]=[CH:12][NH:11][C:10]=2[C:9]2=[N:15][C:16]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[N:17][N:8]2[C:7]1=[O:24])[CH2:2][CH2:3][CH2:4][CH3:5].[Br:25]N1C(=O)CCC1=O.C1(O)C=CC=CC=1>C1COCC1>[Br:25][C:12]1[NH:11][C:10]2[C:9]3=[N:15][C:16]([C:18]4[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=4)=[N:17][N:8]3[C:7](=[O:24])[N:6]([CH2:1][CH2:2][CH2:3][CH2:4][CH3:5])[C:14]=2[N:13]=1

Participants

5

Reactant 3

HCID 996PhenolHCID 67184N-bromobutanimideHCID 1359847084-pentyl-8-phenyl-1,4-dihydro-5H-[1,2,4]triazolo[5,1-i]purin-5-one

Product 1

HCID 1359551382-bromo-4-pentyl-8-phenyl-1,4-dihydro-5H-[1,2,4]triazolo[5,1-i]purin-5-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To the mixture of 4-pentyl-8-phenyl-1,4-dihydro-5H-[1,2,4]triazolo[5,1-i]purin-5-one (25 mg, 0.078 mmol) in THF (5 mL) was added N-Bromosuccinimide (19 mg, 0.11 mmol). After stirring at room temperature for 1 hour, phenol was added to quench the reaction. The reaction mixture was concentrated, and the residue was purified by preparative LCMS (method B) to provide the desired product as white powder. 1HNMR (400 MHz, CD3OD): δ 8.25 (m, 2H), 7.50 (m, 3H), 4.31 (t, J=7.3 Hz, 2H), 1.88 (m, 2H), 1.43 (m, 4H), 0.95 (m, 3H). LCMS calculated for C17H18BrN6O (M+H): 401.1. found: 401.0, 403.0.

Workup

  1. customto quench
  2. customthe reaction
  3. concentrationThe reaction mixture was concentrated
  4. customthe residue was purified by preparative LCMS (method B)

Sources & evidence

ORD record
ord-7836c9419b374f31ab572f9c9fcf1b27
Source dataset
uspto-grants-2011_03
Patent number
US07902205B2

Reaction notes

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