N-bromobutanimide → HCID 135984695, compound

HRID 2374321Notes

Reaction equation

HRID 2374321 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-215d599cff5a452f9c9872bc73de41e3
Source dataset
uspto-grants-2008_12
Patent number
US07462624B2

Reaction notes

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