Bromine → HCID 178461599, compound

HRID 522808Notes

Reaction equation

HRID 522808 reaction equation
[CH3:1][C@H:2]1[CH2:7][O:6][CH2:5][CH2:4][N:3]1[C:8]1[N:16]=[C:15]2[C:11]([N:12]=[CH:13][NH:14]2)=[C:10]([N:17]2[CH2:22][CH2:21][O:20][CH2:19][C@H:18]2[CH3:23])[N:9]=1.[Br:24]Br.[O-]S([O-])(=S)=O.[Na+].[Na+]>C(Cl)Cl>[Br:24][C:13]1[NH:14][C:15]2[C:11]([N:12]=1)=[C:10]([N:17]1[CH2:22][CH2:21][O:20][CH2:19][C@H:18]1[CH3:23])[N:9]=[C:8]([N:3]1[CH2:4][CH2:5][O:6][CH2:7][C@@H:2]1[CH3:1])[N:16]=2

Participants

5

Reactant 3

HCID 24408BromineHCID 24477Sodium ThiosulfateHCID 178461602HCID 178461602, compound

Product 1

HCID 178461599HCID 178461599, compoundYield 46.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

2-((S)-3-Methyl-morpholin-4-yl)-6-((R)-3-methyl-morpholin-4-yl)-9H-purine (786 mg, 2.47 mmol) were dissolved in CH2Cl2 (25 mL). Bromine (0.16 mL, 3.09 mmol) diluted in 2 mL of CH2Cl2 was added slowly within 2 minutes. The reaction mixture was stirred for 6 hours at room temperature. Aqueous Na2S2O3 (10 mL) was added to the reaction mixture, and stirring was continued for 15 minutes. The organic layer was washed with brine and aqueous NaHCO3. Drying over Na2SO4, filtering and concentration under reduced pressure gave a residue, which was purified by column chromatography (40 g SiO2, heptane/EtOAc in a gradient from 2/3 to 4/1) to give the product as a foam (455 mg, 46%).

Workup

  1. additionwas added slowly within 2 minutes
  2. stirringstirring
  3. waitwas continued for 15 minutes
  4. washThe organic layer was washed with brine and aqueous NaHCO3
  5. dry with materialDrying over Na2SO4
  6. filtrationfiltering
  7. concentrationconcentration under reduced pressure
  8. customgave a residue, which
  9. customwas purified by column chromatography (40 g SiO2, heptane/EtOAc in a gradient from 2/3 to 4/1)

Sources & evidence

ORD record
ord-70166902903642bb9a305b9a8fe17d50
Source dataset
uspto-grants-2016_05
Patent number
US09334271B2

Reaction notes

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