Bromine → HCID 178461594, compound

HRID 522813Notes

Reaction equation

HRID 522813 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 178461598HCID 178461598, compound

Product 1

HCID 178461594HCID 178461594, compoundYield 53.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

2,6-Bis-((R)-3-methyl-morpholin-4-yl)-9H-purine (637 mg, 2 mmol) was dissolved in 50 mL of CH2Cl2 and stirred under argon. Bromine (124 μl, 2.4 mmol) was dissolved in 2 mL of CH2Cl2 and added within 2 minutes. The reaction was stirred for 6 hours at room temperature. 5 mL of aqueous Na2S2O3 were added, the mixture was stirred for 15 minutes, and the organic solvents were separated, washed with brine and aqueous NaHCO3, dried over Na2SO4, filtered, and concentrated. The residue was purified by column chromatography (40 g SiO2, heptane/EtOAc in a gradient from 2/3 to 4/1) to give a foam (422 mg, 53%).

Workup

  1. additionadded within 2 minutes
  2. stirringThe reaction was stirred for 6 hours at room temperature
  3. stirringthe mixture was stirred for 15 minutes
  4. customthe organic solvents were separated
  5. washwashed with brine and aqueous NaHCO3
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue was purified by column chromatography (40 g SiO2, heptane/EtOAc in a gradient from 2/3 to 4/1)

Sources & evidence

ORD record
ord-319576340b954a64976ccafcf3097766
Source dataset
uspto-grants-2016_05
Patent number
US09334271B2

Reaction notes

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