N-bromobutanimide → HCID 135984695, compound

HRID 600592Notes

Reaction equation

HRID 600592 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][N:21]=[CH:20][N:19]=3)=[N:17][N:8]2[C:7]1=[O:24])[CH2:2][CH2:3][CH2:4][CH3:5].C(N1C2N=CNC=2C2=NN=C(C3C=CN=CN=3)N2C1=O)CCCC.[Br:49]N1C(=O)CCC1=O>C1COCC1>[Br:49][C:12]1[NH:11][C:10]2[C:9]3=[N:15][C:16]([C:18]4[CH:23]=[CH:22][N:21]=[CH:20][N:19]=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 67184N-bromobutanimideHCID 135984699HCID 135984699, compoundHCID 135984706HCID 135984706, compound

Product 1

HCID 135984695HCID 135984695, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 4-pentyl-8-pyrimidin-4-yl-1,4-dihydro-5H-[1,2,4]triazolo[5,1-i]purin-5-one (14C1) and 6-pentyl-3-pyrimidin-4-yl-6,9-dihydro-5H-[1,2,4]triazolo[3,4-i]purin-5-one (14C2) (25 mg, 0.15 mmol) in THF (5 mL) was added N-bromosuccinimide (19 mg, 0.22 mmol). The reaction mixture was stirred at room temperature for 1 hour, then the reaction was quenched by phenol. After removing the solvent, the residue was purified using preparative LCMS (method B) to yield the pure compound (14D1) and the pure compound 14D2 respectively. LCMS calculated for C15H16BrN8O (M+H): 403.1. found: 403.0, 405.0.

Workup

  1. customthe reaction was quenched by phenol
  2. customAfter removing the solvent
  3. customthe residue was purified
  4. customto yield the pure compound (14D1)

Sources & evidence

ORD record
ord-9fc0514ee5e24af38be576cb5d3d76a7
Source dataset
uspto-grants-2011_03
Patent number
US07902205B2

Reaction notes

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