N-bromobutanimide → 8-Bromo-2-[(1-methylbutyl)oxy]-9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-amine

HRID 1010968Notes

Reaction equation

HRID 1010968 reaction equation
[CH3:1][CH:2]([O:6][C:7]1[N:15]=[C:14]2[C:10]([N:11]=[CH:12][N:13]2[CH:16]2[CH2:21][CH2:20][CH2:19][CH2:18][O:17]2)=[C:9]([NH2:22])[N:8]=1)[CH2:3][CH2:4][CH3:5].C1C(=O)N([Br:30])C(=O)C1>C(Cl)(Cl)Cl.C(Cl)Cl>[Br:30][C:12]1[N:13]([CH:16]2[CH2:21][CH2:20][CH2:19][CH2:18][O:17]2)[C:14]2[C:10]([N:11]=1)=[C:9]([NH2:22])[N:8]=[C:7]([O:6][CH:2]([CH3:1])[CH2:3][CH2:4][CH3:5])[N:15]=2

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 576995892-[(1-Methylbutyl)oxy]-9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-amine

Product 1

HCID 576996498-Bromo-2-[(1-methylbutyl)oxy]-9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-amineYield 102.6%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-[(1-methylbutyl)oxy]-9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-amine (382 mg) in dry chloroform (4.52 mL) at 0° C. was added NBS (234 mg) in a single portion. The reaction was warmed to room temperature and stirred for 5 h. The reaction mixture was taken up in DCM (20 mL) and was washed with water (30 mL). The organics were separated, dried by passing through a hydrophobic frit and concentrated in vacuo to give a green/brown foam (493 mg).

Workup

  1. washwas washed with water (30 mL)
  2. customThe organics were separated
  3. customdried
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a2a424ae08e6409283363eb32e2e87e0
Source dataset
uspto-grants-2011_07
Patent number
US07977344B2

Reaction notes

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