Bromine → HCID 178461551, compound

HRID 876516Notes

Reaction equation

HRID 876516 reaction equation
[CH3:1][C@@H:2]1[O:7][C@H:6]([CH3:8])[CH2:5][N:4]([C:9]2[N:17]=[C:16]3[C:12]([N:13]=[CH:14][NH:15]3)=[C:11]([N:18]3[CH2:23][CH2:22][O:21][CH2:20][CH2:19]3)[N:10]=2)[CH2:3]1.[Br:24]Br.S([O-])([O-])(=O)=S.[Na+].[Na+]>C(Cl)Cl>[Br:24][C:14]1[NH:15][C:16]2[C:12]([N:13]=1)=[C:11]([N:18]1[CH2:19][CH2:20][O:21][CH2:22][CH2:23]1)[N:10]=[C:9]([N:4]1[CH2:5][C@@H:6]([CH3:8])[O:7][C@@H:2]([CH3:1])[CH2:3]1)[N:17]=2

Participants

5

Reactant 3

HCID 24408BromineHCID 24477Sodium ThiosulfateHCID 178461553HCID 178461553, compound

Product 1

HCID 178461551HCID 178461551, compoundYield 34%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-((2S,6R)-2,6-dimethyl-morpholin-4-yl)-6-morpholin-4-yl-9H-purine (860 mg, 2.70 mmol) in CH2Cl2 (5 mL) was added bromine (0.04 mL, 3.24 mmol). The mixture was stirred at ambient temperature for 3 hours. Saturated sodium thiosulfate was added. The aqueous layer was extracted with dichloromethane two times. Organic layers were combined and dried over Na2SO4 and solvent was removed under reduced pressure. The crude was purified by flash column chromatography (0-70% EtOAc/Heptane gradient) to furnish product as an off-white solid (362.1 mg, 34%). LC/MS analysis using method 7, mass (ES+) m/z 399.1 1HNMR (CDCl3): 4.31 (2H, d), 4.09 (4H, brs), 3.74 (4H, m), 3.59 (2H, m), 2.51 (2H, m), 1.18 (6H, d).

Workup

  1. extractionThe aqueous layer was extracted with dichloromethane two times
  2. dry with materialdried over Na2SO4 and solvent
  3. customwas removed under reduced pressure
  4. customThe crude was purified by flash column chromatography (0-70% EtOAc/Heptane gradient)

Sources & evidence

ORD record
ord-a9c8ab7ec9df4d71a66454312e5dee87
Source dataset
uspto-grants-2015_03
Patent number
US08987257B2

Reaction notes

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