N-bromobutanimide → HCID 136047089, compound

HRID 736652Notes

Reaction equation

HRID 736652 reaction equation
[CH2:1]([N:9]1[CH:17]=[N:16][C:15]2[C:14](=[O:18])[NH:13][CH:12]=[N:11][C:10]1=2)[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C1C(=O)N([Br:26])C(=O)C1>O1CCOCC1>[Br:26][C:17]1[N:9]([CH2:1][CH2:2][C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:10]2[N:11]=[CH:12][NH:13][C:14](=[O:18])[C:15]=2[N:16]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 1354910399-Phenethyl-1,9-dihydro-purin-6-one

Product 1

HCID 136047089HCID 136047089, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
105 °C

Procedure

To a solution of purinone from step 2 (0.29 g, 1.21 mmol) from above reaction in dioxane (0.1M) is added NBS (0.32 g, 1.81 mmol). The resulting reaction mixture was heated to 105° C. until HPLC shows consumption of starting material (ca. 2 h). The reaction was cooled to rt and purified by MPLC using a solvent gradient of 0-20% MeOH/CH2Cl2. The product containing fractions were collected and concentrated to provide the desired product (0.22 g, 57% yield). 1H NMR (DMSO-d6) δ 12.49 (s, 1H), 8.08 (s, 1H), 7.30-7.21 (m, 3H), 7.10-7.04 (m, 2H), 4.36 (t, J=7.0 Hz, 2H), 3.17 (t, J=7.3 Hz, 2H).

Workup

  1. customThe resulting reaction mixture
  2. customconsumption of starting material (ca. 2 h)
  3. temperatureThe reaction was cooled to rt
  4. custompurified by MPLC
  5. additionThe product containing fractions
  6. customwere collected
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-52a179a9bd4b4336b79416a4113b5c75
Source dataset
uspto-grants-2009_09
Patent number
US07595401B2

Reaction notes

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