Water → HCID 59252576, compound

HRID 527822Notes

Reaction equation

HRID 527822 reaction equation
[Br:1]N1C(=O)CCC1=O.[CH3:9][C@@H:10]([NH:14][C:15]1[N:23]=[C:22]2[C:18]([N:19]=[CH:20][N:21]2[CH:24]2[CH2:29][CH2:28][CH2:27][CH2:26][O:25]2)=[C:17]([NH2:30])[N:16]=1)[CH2:11][CH2:12][CH3:13].O>C(Cl)(Cl)Cl>[Br:1][C:20]1[N:21]([CH:24]2[CH2:29][CH2:28][CH2:27][CH2:26][O:25]2)[C:22]2[C:18]([N:19]=1)=[C:17]([NH2:30])[N:16]=[C:15]([NH:14][C@H:10]([CH3:9])[CH2:11][CH2:12][CH3:13])[N:23]=2

Participants

5

Reactant 3

HCID 962WaterHCID 67184N-bromobutanimideHCID 59252645HCID 59252645, compound

Product 1

HCID 59252576HCID 59252576, compoundYield 29.6%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

N-Bromosuccinimide (2.08 g, 11.69 mmol) was added portionwise to a stirred solution of N2-[(1R)-1-methylbutyl]-9-(tetrahydro-2H-pyran-2-yl)-9H-purine-2,6-diamine (2.27 g, 7.46 mmol) in chloroform (30 ml) at 0° C. under at atmosphere of nitrogen. The reaction mixture was allowed to stir for 1.5 hours when chloroform (20 ml) and water (50 ml) were added. After mixing the layers were separated using a hydrophobic frit, the aqueous layer was washed with an additional portion of chloroform and the combined organic extracts were evaporated. The residue was dissolved in dichloromethane and purified on a 110 g aminopropyl (NH2) cartridge using a 0-100% ethyl acetate in cyclohexane gradient over 40 mins. The appropriate fractions were combined and evaporated in vacuo to give the title compound as an off-white foam (0.846 g).

Workup

  1. additionwere added
  2. additionAfter mixing the layers
  3. customwere separated
  4. washthe aqueous layer was washed with an additional portion of chloroform
  5. customthe combined organic extracts were evaporated
  6. dissolutionThe residue was dissolved in dichloromethane
  7. custompurified on a 110 g aminopropyl (NH2) cartridge
  8. customover 40 mins
  9. customevaporated in vacuo

Sources & evidence

ORD record
ord-ba8e0136a5b74645b9554daa54c4b16f
Source dataset
uspto-grants-2016_05
Patent number
US09346806B2

Reaction notes

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